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[ CAS No. 670-98-4 ] {[proInfo.proName]}

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Chemical Structure| 670-98-4
Chemical Structure| 670-98-4
Structure of 670-98-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 670-98-4 ]

CAS No. :670-98-4 MDL No. :MFCD00674051
Formula : C7H8O2S Boiling Point : -
Linear Structure Formula :- InChI Key :PSNSVDSRLUYDKF-UHFFFAOYSA-N
M.W : 156.20 Pubchem ID :2759784
Synonyms :

Calculated chemistry of [ 670-98-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.93
TPSA : 45.51 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.02
Log Po/w (XLOGP3) : 0.94
Log Po/w (WLOGP) : 2.22
Log Po/w (MLOGP) : 1.6
Log Po/w (SILICOS-IT) : 0.6
Consensus Log Po/w : 1.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.71
Solubility : 3.03 mg/ml ; 0.0194 mol/l
Class : Very soluble
Log S (Ali) : -1.48
Solubility : 5.14 mg/ml ; 0.0329 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.53
Solubility : 0.463 mg/ml ; 0.00296 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.6

Safety of [ 670-98-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 670-98-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 670-98-4 ]

[ 670-98-4 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 670-98-4 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 67-56-1 ]
  • [ 945-51-7 ]
  • 2
  • [ 670-98-4 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 945-51-7 ]
  • 3
  • [ 670-98-4 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 108-98-5 ]
  • 4
  • [ 67-56-1 ]
  • [ 108-98-5 ]
  • [ 670-98-4 ]
YieldReaction ConditionsOperation in experiment
93% General procedure: Solid N-bromosuccinimide powder (2 equiv) was added in one portion to a 0° C., methanol:dichloromethane solution (1:1 by volume) of the thiol (1 equiv). The cold bath was removed and, after 1 hour, the mixture was poured into 0° C., saturated NaHCO3 solution. The biphasic mixture was transferred to a separation funnel and shaken until discoloration. The phases were separated and the aqueous layer was extracted with dichloromethane (×3). The combined organic extract was washed with brine, dried (Na2SO4), and concentrated to afford a yellowish crude sulfinate. The crude sulfinate was purified by filtration through a SiO2 plug (10×50 mm) to afford pure methyl sulfinate. Methyl benzenesulfinate (compound 4a) was prepared from thiophenol (4 g, 36.4 mmol) according to the general sulfinate synthesis affording 5.27 g of compound 4a (93percent) as a colorless oil after purification by SiO2 flash chromatography (hexanes:Et2O gradient, 100:0 to 90:10)
87% With eosin; at 20℃; for 1.5h;Irradiation; General procedure: A round bottom flask was charged with thiol RSH 1(a?r)(1.0 mmol), eosin Y (2 mol percent), alcohol (ROH) 2a?f (3 mL) and the contents were stirred in open air under irradiationwith Luxeon Rebel high power green LEDs [2.50 W, lambda =535 nm] at room temperature for the time specified in (Table 1). After the completion of reaction as monitored byTLC (preparative TLC), the resulting mixture was filtered and washed with ethyl acetate, and then concentrated to remove the excess of solvent under vacuum. The organic phase was dried over anhydrous magnesium sulfate and purified with TLC (preparative TLC silica gel). The eluentused was petroleum ether: ethyl acetate (20 : 1; v / v) to gavethe desire product 3a-r. with excillent yields (75?95 percent).
  • 5
  • [ 67-56-1 ]
  • [ 873-55-2 ]
  • [ 670-98-4 ]
YieldReaction ConditionsOperation in experiment
84% With sulfuric acid; In dichloromethane; at 25℃; for 8.5h;Molecular sieve; General procedure: In a test tube containing the appropriate sodium salt of sulfinic acid, 1a-d (1 mmol) was added the appropriate alcohol (1 mL) followed by dichloromethane (4 mL) [For more complex alcohols, 3 equiv. (3 mmol) of alcohol were used]. Under stirring, sulfuric acid (106 mL, 2 equiv.) was added and after 30 min of reaction, powdered 4 A molecular sieves (200 mg) was added. The mixture was stirred for the time indicated on Table 2 and then diluted with dichloromethane (10 mL) and transferred to a separation funnel. The organic phase was then washed with water (2 x 20 mL), dried over anhydrous MgSO4 and filtered through a pad of silica. The solvents were removed in vacuo and the resulting crude product was further purified by flash column chromatography [hexanes:EtOAc (98:2)].
  • 7
  • [ 67-56-1 ]
  • [ 117410-68-1 ]
  • [ 670-98-4 ]
  • [ 59899-89-7 ]
  • 8
  • [ 4972-29-6 ]
  • [ 13165-72-5 ]
  • [ 670-98-4 ]
  • 9
  • [ 64-17-5 ]
  • [ 670-98-4 ]
  • [ 1859-03-6 ]
  • 10
  • [ 629-05-0 ]
  • [ 670-98-4 ]
  • [ 146916-38-3 ]
  • 11
  • [ 5771-32-4 ]
  • [ 670-98-4 ]
  • [ 93069-39-7 ]
  • 12
  • [ 670-98-4 ]
  • [ 1072-77-1 ]
  • [ 98877-49-7 ]
  • 13
  • [ 670-98-4 ]
  • [ 7680-12-8 ]
  • [ 111119-47-2 ]
  • 14
  • [ 670-98-4 ]
  • [ 571-31-3 ]
  • [ 111119-49-4 ]
  • 15
  • [ 670-98-4 ]
  • [ 67300-99-6 ]
  • [ 49833-32-1 ]
  • 16
  • [ 670-98-4 ]
  • [ 87295-66-7 ]
  • [ 87295-68-9 ]
  • 17
  • [ 670-98-4 ]
  • [ 87295-65-6 ]
  • [ 87309-96-4 ]
  • 18
  • [ 670-98-4 ]
  • [ 117106-95-3 ]
  • C22H28O2S3 [ No CAS ]
  • 19
  • [ 670-98-4 ]
  • [ 68197-11-5 ]
  • [ 73509-29-2 ]
  • 20
  • [ 670-98-4 ]
  • [ 111264-15-4 ]
  • [ 111263-94-6 ]
  • 21
  • [ 670-98-4 ]
  • [ 149705-59-9 ]
  • [ 149705-58-8 ]
  • 22
  • [ 67-56-1 ]
  • [ 108-98-5 ]
  • [ 1212-08-4 ]
  • [ 670-98-4 ]
  • [ 882-33-7 ]
  • 24
  • [ 933803-10-2 ]
  • [ 670-98-4 ]
  • 3-benzenesulfinyl-1-benzyl-6-phenyl-piperidin-2-one [ No CAS ]
  • 25
  • [ 933803-09-9 ]
  • [ 670-98-4 ]
  • 3-benzenesulfinyl-6-benzyl-1-phenyl-piperidin-2-one [ No CAS ]
  • 26
  • [ 933803-11-3 ]
  • [ 670-98-4 ]
  • 3-benzenesulfinyl-1,6-dibenzyl-piperidin-2-one [ No CAS ]
  • 27
  • [ 933803-12-4 ]
  • [ 670-98-4 ]
  • 3-benzenesulfinyl-1-benzyl-6-phenethyl-piperidin-2-one [ No CAS ]
  • 28
  • [ 670-98-4 ]
  • [ 116805-89-1 ]
  • [ 1027035-96-6 ]
  • 29
  • [ 670-98-4 ]
  • [ 227083-14-9 ]
  • 2-benzenesufinyl-6,7-benzobicyclo[3.2.0]hept-6-en-2-one [ No CAS ]
  • 30
  • benzenesulfinic acid 2-isopropyl-5-methyl-cyclohexyl ester [ No CAS ]
  • [ 670-98-4 ]
  • 31
  • [ 670-98-4 ]
  • 18-methyl-16ξ-phenylsulfoxide-4-estren-3,17-dione [ No CAS ]
  • 32
  • [ 670-98-4 ]
  • 2-benzenesulfinyl-6,7-benzobicyclo[3.2.0]hept-6-en-2-one tozylhydrazone [ No CAS ]
  • 33
  • [ 670-98-4 ]
  • [ 184848-17-7 ]
  • 34
  • [ 670-98-4 ]
  • (R)-4-((R)-Benzenesulfinyl)-5,5-dimethyl-2-methylene-hexanoic acid methyl ester [ No CAS ]
  • 35
  • [ 670-98-4 ]
  • (R)-4-((S)-Benzenesulfinyl)-5,5-dimethyl-2-methylene-hexanoic acid methyl ester [ No CAS ]
  • 38
  • [ 670-98-4 ]
  • [ 93069-43-3 ]
  • 39
  • [ 670-98-4 ]
  • [ 93069-40-0 ]
  • 40
  • [ 39574-20-4 ]
  • [ 670-98-4 ]
  • 41
  • [ 24244-60-8 ]
  • [ 670-98-4 ]
  • 43
  • [ 670-98-4 ]
  • [ 98877-47-5 ]
  • 44
  • [ 670-98-4 ]
  • [ 98877-50-0 ]
  • 48
  • [ 670-98-4 ]
  • [ 116205-46-0 ]
  • 49
  • [ 670-98-4 ]
  • [ 116205-47-1 ]
  • 50
  • [ 67-56-1 ]
  • [ 7304-68-9 ]
  • [ 670-98-4 ]
  • 51
  • [ 670-98-4 ]
  • [ 865088-75-1 ]
YieldReaction ConditionsOperation in experiment
Step 2: 1- (3-Chloro-4-fluorobenzyl)-5, 6-dihydropyridin-2 (1H)-one; 1- (3-Chloro-4-fluorobenzyl) piperidin-2-one (340g, 1.41 mol) was dissolved in THF (5 L) and cooled to-20 °C under nitrogen. LHMDS (3. 09L, 3. 09 mol, 1M in THF) was added over 40 minutes keeping the temperature at-20 °C and aged for 1 hr at-20 °C. The methyl benzene sulfonate (231 mL, 1.69 mol) was added over 30 minutes, again keeping the internal temperature at-20 °C. The reaction was aged for 30 minutes at-20 °C and LCMS showed the reaction complete. The reaction mixture was diluted with 4L EtOAc and washed with four 2L portions of distilled H20. The organic layer was concentrated and the residue was dissolved in 4L toluene. Na2CO3 (500g) was added and the reaction heated to 100 °C for 1 hour. LCMS showed the reaction complete. The residue was diluted with 4 L EtOAc and washed with four 2L portions of distilled water. The organic layer was concentrated and the residue purified by flash chromatography on silica eluting with a gradient of 0-60percent EtOAc/heptane. The product was isolated as an oil. 1H NMR (400 MHz, CDC13) 8 7.3 (m, 1H), 7.15 (m, 1H), 7.1 (t, 1H), 6.6 (m, 1H), 6. 0 (m, 1H), 4.55 (s, 2H), 3.33 (t, 2H), 1.38 (m, 2H) ppm. (ES MS M+1 = 240.13)
  • 52
  • [ 670-98-4 ]
  • C18H15ClFNOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Step 2: Preparation of an unsaturated sulfide of formula 1; 1- (3-Chloro-4-fluorobenzyl) piperidin-2-one (25g) was dissolved in THF (250 mL) and cooled to-20 degrees C under nitrogen atmosphere. LHMDS (204 mL, 1M in THF) was added over 40 minutes at-20 to-30°C and aged for 1 hour at-20°C. Methyl benzene sulfinate (17.78 g) was added over 30 minutes, again keeping the internal temperature at-20°C. The reaction was aged for 30 minutes at- 20°C at which time LC showed the reaction to be complete. The reaction mixture was then quenched with water (100 mL) and diluted with EtOAc (300 mL). After phase cut, the organic layer was washed with HCl 2N (2 x 100 mL). The organic layer was then washed with brine (2 x 100 mL), dried under MgS04 followed by solvent switch to DCM (600 mL; final volume 400 mL). To this solution was added acetic anhydride (11.6 rnL) and MeS03H (3.07 mL). The solution was then aged at room temperature overnight. The reaction was quenched with water (300 mL) and cooled to 0°C. The slurry obtained was then carefully basified to pH=8 with solid Na2CO3. The organic layer obtained after phase cut was then washed with brine and dried under MgSO4. After evaporation of solvents, the title unsaturated sulfide 1 was obtained as an oil which solidified on standing. The title sulfide 1 can be crystallized from MeOH.
  • 53
  • [ 670-98-4 ]
  • [ 865088-39-7 ]
YieldReaction ConditionsOperation in experiment
Step 2: 1- (4-fluorobenzyl)-3- (phenylsulfinyl) piperidin-2-one; To a cooled (0 °C) solution of 1- (4-fluorobenzyl) piperidine (5. 0g, 24.1 mmol) in anhydrous THF (100 mL) was added lithium bis (trimethylsilyl) amide (1.0 M in THF, 53 rnL, 53 mmol) dropwise, and the solution was stirred for one half hour. The solution was treated with methyl benzene sulfinate (5.65g, 36.1 mmol) in anhydrous THF (3 mL) dropwise. After 30 minutes at 0 °C, the resultant mixture was quenched with water and partitioned between 10percent KHIS04 and CHC13, the layers separated and the aqueous extracted several more times with CHC13. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum to afford 1-(4-fluorobenzyl)-3-(phenylsulfinyl) piperidin-2-one as a waxy solid that was taken on to the next step. ES MS M+1 = 332
  • 54
  • 18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5-estren-17-one [ No CAS ]
  • [ 670-98-4 ]
  • [ 64133-03-5 ]
  • [ 769938-73-0 ]
  • [ 769938-75-2 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In tetrahydrofuran; at 20℃; for 2.16h;Product distribution / selectivity; Potassium tert.-butylate (0.79 g, 7.06 mmol) was added under an inert atmosphere with vigorous stirring to a solution of compound (3a) (0.65 g, 1.73 mmol) in anhydrous tetrahydrofuran (14.2 ml). The reaction mixture was stirred at ambient temperature for 10', then <strong>[670-98-4]methyl benzenesulfinate</strong> (0.91 ml, d 1.194, 6.96 mmol) was added and the reaction composition was stirred for 2 hours at ambient temperature. After this period, ethyl acetate (20 ml) is added and the organic phase is washed successively with a solution of sodium chloride (3x30 ml), water (30 ml) and then with a saturated sodium chloride solution (30 ml). The organic phase is dehydrated over sodium sulfate, filtered and concentrated down to a residue under reduced pressure. The resultant oily product (5a) (0.850 g; 1.71 mmol) is used in the subsequent step without purification. Mass fragmentation analysis (m/z): 498 (m+1); 497 (m+/.); 371 (m-126); 370 (m-127) IR (1percent KBr)= 3449.9 cm-1, 2954.9 cm-1, 2868.9 cm-1, 1735.9 cm-1 (C=O st); 1129.6, 1106.5, 1093.8 and 1048.7 cm-1 (S=O st).
  • 55
  • [ 109-97-7 ]
  • [ 13754-86-4 ]
  • [ 670-98-4 ]
  • [ 766-80-3 ]
  • [ 247096-45-3 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; EXAMPLE 4 Preparation of 1-(3-Chlorophenyl(methyl))-4-hydroxyindole 1-(3-chlorobenzyl)-4-oxo-4,5,6,7-tetrahydroindole was prepared from 1,5,6,7-tetrahydro-4H-indol-4-one and 3-chlorobenzylbromide using methodology common to the art. The pyrrole (0.5 g, 1.9 mmol) was dissolved in tetrahydrofuran (2.5 mL). Sodium hydride (0.18 g, 4.4 mmol) was added. After 5 minutes, <strong>[670-98-4]methyl benzenesulfinate</strong> (0.48 g, 3.1 mmol) was added. The color of the mixture darkened to red as gas evolution was observed. The mixture was stirred for 1 hour. Thin layer chromatography indicated complete consumption of starting material (sulfoxides, Rf 0.11; 1/1 hexane/ethyl acetate). The reaction mixture was quenched with water, stirred for 10 minutes, and diluted with chloroform. The solution was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and evaporated to give an orange oil. The oil was dissolved in dioxane (5 mL) and refluxed for 3 hours at which time the sulfoxides were no longer observed by thin layer chromatography. The reaction mixture was cooled to room temperature and a solution of lithium hydroxide (85 mg) in water (2 mL) was added. The solvent was evaporated and the residue was dissolved in chloroform. The solution was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and evaporated to give an orange oil.
  • 56
  • 9-benzyl-4-hydroxy-6-oxy carbazole [ No CAS ]
  • [ 670-98-4 ]
  • [ 247096-40-8 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; B. Preparation of 9-benzyl-4-hydroxy-6-methoxy carbazole The compound of part A, above (0.2 g, 0.65 mmol), was dissolved in tetrahydrofuran (2 mL). Sodium hydride (0.06 g, 1.5 mmol) was added. After 5 minutes, <strong>[670-98-4]methyl benzenesulfinate</strong> (0.16 g, 1 mmol) was added. After 30 minutes, the brown mixture was warmed until gas evolution was sustained. The mixture became a thick paste. tetrahydrofuran (2 mL) was added and the resultant slurry was refluxed for 20 minutes. TLC indicated consumption of starring material (diastereomeric sulfoxides, Rf 0.1, 0.14; 1/1 hexane/ethyl acetate). The reaction mixture was quenched with water, stirred for 5 minutes, and diluted with chloroform. The solution was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and evaporated to give an orange oil. The oil was dissolved in dioxane (5 mL) and refluxed for 1 hour at which time the sulfoxides were no longer observed by thin layer chromatography. The reaction mixture was cooled to room temperature and diluted with chloroform. The solution was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and evaporated. Column chromatography with 80percent chloroform in hexane to 100percent chloroform provided 0.13 g of an amber solid. (65percent yield) Thin layer chromatography Rf 0.27 (20percent EtOAc in hexane);
  • 57
  • [ 670-98-4 ]
  • [ 36767-62-1 ]
  • [ 51627-86-2 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; EXAMPLE 5 Preparation of 1-Phenyl-3-methyl-4-hydroxy Indazole Starting material 1-phenyl-3-methyl-4-oxo-4,5,6,7-tetrahydroindazole (0.2 g, 0.9 mmol, prepared as described by Peet, N. P.; LeTourneau, M. E. Heterocycles 1991, 32, 41, was dissolved in tetrahydrofuran (2 mL). Sodium hydride (0.07 g, 1.6 mmol) was added. After 5 minutes, <strong>[670-98-4]methyl benzenesulfinate</strong> (0.17 g, 1.1 mmol) was added. The color of the mixture changed to pink as gas evolution was observed. The mixture was stirred for 45 minutes. Thin layer chromatograhy indicated complete consumption of starting material (sulfoxides, Rf 0.27, 0.33; 1/1 hexane/ethyl acetate). The reaction mixture was quenched with water, stirred for 1 hour, and diluted with dichloromethane. The solution was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and evaporated to give an orange oil. The oil was dissolved in dioxane (2 mL) and refluxed for 1 hour at which time the sulfoxides were no longer observed by TLC. The reaction mixture was cooled to room temperature and a solution of lithium hydroxide (38 mg) in water (2 mL) was added. The solvent was evaporated and the residue was dissolved in dichloromethane. The solution was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and evaporated to give an orange solid. Column chromatography with 20percent ethyl acetate in hexane provided 0.14 g of a white solid. (70percent yield) TLC Rf 0.25 (20percent EtOAc in hexane);
  • 58
  • [ 247096-46-4 ]
  • [ 670-98-4 ]
  • [ 247096-43-1 ]
YieldReaction ConditionsOperation in experiment
60% With NaH; In tetrahydrofuran; water; ethyl acetate; EXAMPLE 7 Preparation of 1-Phenylmethyl-4-hydroxy-6-methyl Indole To a solution of the 1-phenylmethyl-4-oxo-6-methyl-4,5,6,7-tetrahydroindole (1.0 g, 3.5 mmol) in 5 mL tetrahydrofuran was added NaH (0.3 g, 7.5 mmol) in portions. The resulting mixture was stirred 10 min and <strong>[670-98-4]methyl phenylsulfinate</strong> (0.7 g, 4.5 mmol) was added in one portion. The mixture was stirred for 45 minutes and then warmed (35-45° C.) for 30 minutes. Water (5 mL) was added and the resulting mixture was stirred for 10 minutes. The intermediate sulfoxide was extracted with toluene. The tolurene solution was dried over sodium sulfate, filtered and concentrated to approximately 50 mL. The mixture was heated to reflux for 45 min. The solution was cooled to room temperature and washed with sodium bicarbonate and brine. The organic solution was dried over Na2SO4, filtered and concentrated to an oil. The residue was purified by silica gel chromatography (10percent ethyl acetate in hexanes) to give 0.60 g of the desired product (60percent).
  • 59
  • [ 670-98-4 ]
  • [ 3959-05-5 ]
  • [ 865-33-8 ]
  • [ 257940-07-1 ]
YieldReaction ConditionsOperation in experiment
In toluene; Part A. Preparation of [[2-ethyl-1-(2-bromo-phenylmethyl)-1H-indol-4-yl]oxy]acetic acid tert-butyl ester 2-Ethyl-1,5,6,7-tetrahydro-1-(2-bromo-phenylmethyl)-4H-indol-4-one (6.64 g), obtained according to Example 7, Part C, using 2-bromobenzyl amine, was dissolved in 20 mL of toluene, treated with potassium methoxide (5.75 g) and a solution of methyl benzene sulfinate in 3 mL of toluene added. After warming the solution to 30 to 40 degrees for 30 minutes, it was allowed to cool to room temperature and kept there for 2 hours. The solution was cooled to 10 degrees, diluted with toluene, water was added and the toluene layer separated. The toluene layer was heated to 80-85 degrees for 3 hours. The toluene was flash evaporated and the residue subject to flash chromatography on silica eluding with 4/1 chloroform/ethyl acetate to provide 4.5 g of phenolic intermediate.
  • 60
  • [ 257939-97-2 ]
  • [ 670-98-4 ]
  • [ 172733-13-0 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; toluene; Part D. Preparation of 2-ethyl-4-hydroxy-1-(2-phenyl-phenylmethyl)-1H-indole 2-Ethyl-1,5,6,7-tetrahydro-1-(2-phenyl-phenylmethyl)-4H-indol-4-one (2.17 g, 0.0066 mol) dissolved in 10 mL of tetrahydrofuran was added to a slurry of sodium hydride (0.58 g) in 3 mL of tetrahydrofuran and the mixture was stirred for 15 min at room temperature. Methyl benzene sulfinate (1.13 g) was added and the solution stirred overnight. The reaction mixture was poured into water, the pH adjusted to 6 with acetic acid and extracted with toluene. The organic layer was separated, washed with water and brine, dried with sodium sulfate, concentrated, taken up in toluene (80 mL) and heated at reflux for 1.5 h. After cooling, the mixture was concentrated, dissolved in ether (100 mL), washed with saturated sodium bicarbonate solution, dried over sodium sulfate, concentrated and purified by flash chromatography on silica eluding with 10:1 hexane/ethyl acetate to afford 0.85 g of subtitled material.
  • 61
  • trans-3-methyl-4-(2-propenyl)cyclohexanone [ No CAS ]
  • [ 670-98-4 ]
  • 5-methyl-4-(2-propenyl)-2-phenylsulfenylcyclohexanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium chloride; In 1,2-dimethoxyethane; PREPARATION Q 5-Methyl-4-(2-propenyl)-2-phenylsulfenylcyclohexanone To a 0° C. mixture of 16.9 g. (0.109 mole) of <strong>[670-98-4]methyl benzenesulfinate</strong> and 8.68 g. (0.217 mole) of potassium hydride in 100 ml. of dimethoxyethane was slowly added a solution of 15.0 g. (0.0987 mole) of trans-3-methyl-4-(2-propenyl)cyclohexanone in 50 ml. of dimethoxyethane. The reaction was stirred 30 minutes longer at 0° C. and then cautiously added to 500 ml. of ice-saturated sodium chloride and 45 ml. 6 N hydrochloric acid. The quenched reaction mixture was extracted once with 300 ml. ether and once with 200 ml. dichloromethane. The organic extract was dried over magnesium sulfate and evaporated to give a quantitative yield of the title compound as a semisolid mixture of axial and equatorial sulfenates. Crystallization from ether yields 7.8 g. of pure axial sulfenate.
  • 62
  • [ 670-98-4 ]
  • [ 70434-17-2 ]
  • 6-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohept-3-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With calcium carbonate; In 1,2-dimethoxyethane; water; toluene; PREPARATION U 6-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohept-3-en-1-one To a 0° C. slurry of 2.19 g. (0.055 mole) of potassium hydride in 20 ml. of dimethoxyethane is added 4.32 g. (0.028 mole) of <strong>[670-98-4]methyl phenylsulfinate</strong>. To the resultant mixture is added, dropwise over a 30 minute period, a solution of 9.82 g. (0.024 mole) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]cycloheptanone in 20 ml. of dimethoxyethane. The reaction is stirred one hour at 0° C. and then quenched by dropwise addition of 1 ml. of water. The quenched reaction mixture is added to 15 ml. ether-15 ml. dichloromethane-12.5 ml. 6 N HCl-40 ml. saturated sodium chloride. The aqueous phase is extracted with another 15 ml. portion of dichloromethane. The combined organic extract is dried over magnesium sulfate and evaporated to a semisolid. It is used as is in the next step. The crude product thus obtained is mixed with 2.68 g. (0.0268 mole) of calcium carbonate in 100 ml. of toluene and heated at 110° C. for 30 minutes. The reaction mixture is cooled, filtered through magnesium sulfate and the filtrate evaporated on a rotovapor to yield an oil which was purified via column chromatography on 500 g. of silica gel eluted with 39percent ether-hexane to yield the title compound.
  • 63
  • [ 246513-43-9 ]
  • [ 670-98-4 ]
  • [ 246513-44-0 ]
YieldReaction ConditionsOperation in experiment
2.31 g (81%) In 1,4-dioxane; mineral oil; (b) To a solution of the 9-[(phenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one (2.87 g, 8.61 mM) in 29 ml dioxane was added 60percent sodium hydride in mineral oil (0.79 g, 19.8 mM). The reaction was stirred 8 minutes, then <strong>[670-98-4]methyl benzenesulfinate</strong> (1.80 ml, 13.8 mM) was added. The reaction was stirred an additional 1.5 h, then diluted with 43 ml dioxane and 1.13 ml acetic acid. The mixture was refluxed 1 h, diluted with ethyl acetate, and extracted with sat'd NaHCO3two times, then with brine. After drying (NaSO4), evaporation in vacuo afforded 4.90 g. The mixture was purified by column chromatography on silica gel (elution with toluene/methylene chloride) to afford 2.31 g (81percent) of the 9-[(phenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole. 1H NMR (DMSO-d6) delta 10.25 (s, 1H), 7.7 (d, 1H, J=8 Hz), 7.4 (t, 1H, J=8 Hz), 7.4-7.0 (m, 8H), 6.6 (d, 1H, J=8 Hz), 5.6 (s, 2H), and 3.8 (s, 3H). IR (CHCl3, cm-l) 1723, 1685, 1621, 1597, 1568, 1496, 1453, 1442, 1392, 1286, 1267, 1156, and 1138. MS (ES) m/e 330, 332.
2.31 g (81%) In 1,4-dioxane; mineral oil; (b) To a solution of the 9-[(phenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one (2.87 g, 8.61 mM) in 29 ml dioxane was added 60percent sodium hydride in mineral oil (0.79 g, 19.8 mM). The reaction was stirred 8 minutes, then <strong>[670-98-4]methyl benzenesulfinate</strong> (1.80 ml, 13.8 mM) was added. The reaction was stirred an additional 1.5 h, then diluted with 43 ml dioxane and 1.13 ml acetic acid. The mixture was refluxed 1 h, diluted with ethyl acetate, and extracted with sat'd NaHCO3 two times, then with brine. After drying (NaSO4), evaporation in vacuo afforded 4.90 g. The mixture was purified by column chromatography on silica gel (elution with toluene/methylene chloride) to afford 2.31 g (81percent) of the 9-[(phenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole. 1H NMR (DMSO-d6) delta 10.25 (s, 1H), 7.7 (d, 1H, J=8 Hz), 7.4 (t, 1H, J=8 Hz), 7.4-7.0 (m, 8H), 6.6 (d, 1H, J=8 Hz), 5.6 (s, 2H), and 3.8 (s, 3H). IR (CHCl3, cm-1) 1723, 1685, 1621, 1597, 1568, 1496, 1453, 1442, 1392, 1286, 1267, 1156, and 1138. MS (ES) m/e 330, 332. Elemental Analyses for C21H17NO3: Calculated: C, 76.13; H, 5.14; N, 4.23. Found: C, 75.90; H, 5.20; N, 4.46.
  • 64
  • 9-[(3-methylphenyl)methyl]-2-methyl-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one [ No CAS ]
  • [ 670-98-4 ]
  • 9-[(3-methylphenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.92 g (66%) In 1,4-dioxane; mineral oil; B. 9-[(3-Methylphenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy Carbazole To a solution of 9-[(3-methylphenyl)methyl]-5-carbomethoxy-2-methyl-1,2-dihydrocarbazol-4(3H)-one (1.41 g, 3.89 mM) in 13 ml dioxane was added 60percent sodium hydride in mineral oil (0.36 g, 8.95 mM). The reaction was stirred 6 minutes, then <strong>[670-98-4]methyl benzenesulfinate</strong> (0.81 ml, 6.22 mM) was added. The reaction was stirred an additional 6 hours, then diluted with 20 ml dioxane and 0.51 ml acetic acid. The mixture was refluxed 30 minutes, diluted with ethyl acetate, and extracted with saturated NaHCO3, brine, then water. After drying (NaSO4), evaporation in vacuo afforded 2.30 g. The mixture was purified by column chromatography on silica gel (elution with toluene/methylene chloride) to afford 0.92 g (66percent) of 9-[(3-methylphenyl)methyl]-2-methyl-4-hydroxy-5-carbomethoxy carbazole. 1H NMR (CDCl3) delta 10.45 (s, 1H), 8.0 (d, J=8 Hz, 1H), 7.55 (d, J=8 Hz, 1H), 7.4 (dd, J=8 and 8 Hz, 1H), 7.4 (dd, J=8 and 8 Hz, 1H), 7.05 (d, J=8 HZ, 1H), 6.9 (s, 1H), 6.85 (d, J=8 Hz, 1H), 6.75 (s, 1H), 6.7 (s, 1H), 5.45 (s, 2H), 4.1 (s, 3H), 2.4 (s, 3H), 2.25 (s, 3H). MS (ES) m/e 328, 360.
  • 65
  • 9-[(2,6-difluorophenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one [ No CAS ]
  • [ 670-98-4 ]
  • 9-[(2,6-difluorophenyl)methyl]-4-hydroxy-5-carbomethyoxy carbazole [ No CAS ]
  • 9-[(2,6-difluorophenyl)methyl]-4-hydroxy-5-carbomethoxy carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
480 mg (47%) In 1,4-dioxane; B. 9-[(2,6-Difluorophenyl)methyl]-4-hydroxy-5-carbomethoxy Carbazole A 60percent oil dispersion of sodium hydride (257 mg, 6.42 mM) was added to a solution of the 9-[(2,6-difluorophenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one (1.03 g, 2.79 mM) in 7 mL of dioxane at room temperature. After 5 minutes <strong>[670-98-4]methyl benzenesulfinate</strong> (0.6 mL, 4.46 mM) was added and the mixture stirred at room temperature for 1.75 hours. The mixture was diluted with 10 mL dioxane, then glacial acetic acid (0.37 mL, 6.42 mM) was added. The resultant mixture was refluxed for 45 min, cooled to room temperature, diluted with ethyl acetate, washed three times with saturated NaHCO3, and saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (elution with toluene) to afford 480 mg (47percent) of the 9-[(2,6-difluorophenyl)methyl]-4-hydroxy-5-carbomethyoxy carbazole as a yellow solid. 1H NMR (CDCl3) delta 10.15 (s, 1H), 7.95 (d, 1H, J=8 Hz), 7.5 (d, 1H, J=8 Hz), 7.5-7.0 (m, 4H), 6.9-6.8 (m, 3H), 5.6 (s, 2H), and 4.1 (s, 3H). IR (KBr, cm-1) 3040 and 1682. MS (ES) m/e 366, 368. Elemental Analyses for C21H15NO3F2: Calculated: C, 68.66; H, 4.12; N, 3.81. Found: C, 69.48; H, 4.07; N, 4.11.
  • 66
  • [ 247903-82-8 ]
  • [ 670-98-4 ]
  • 9-[(2-pyridyl)methyl]-4-hydroxy-5-carbomethyoxy carbazole [ No CAS ]
  • [ 247903-83-9 ]
YieldReaction ConditionsOperation in experiment
470.0 mg (94%) In 1,4-dioxane; acetic acid; mineral oil; B. 9-[(2-Pyridyl)methyl]-4-hydroxy-5-carbomethoxy Carbazole A solution of the 9-[(2-pyridyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one (500 mg, 1.50 mmol) in 2 mL of dioxane was treated with sodium hydride (140 mg; 3.50 mmol; 60percent dispersion in mineral oil) and the mixture stirred for 15 minutes. Methyl benzenesulfinate (0.32 mL; 2.45 mmol) was added dropwise and the reaction stirred at room temperature. After 0.5 hours, gas evolution began and the reaction turned dark brown. The mixture was stirred until tlc indicated complete consumption of starting material (1 hour) at which time glacial acetic acid (0.20 mL; 3.50 mmol) was added. An additional 2 mL of dioxane was added to assist stirring and the mixture was heated to mild reflux for 1 hour. The reaction was cooled and diluted with EtOAc (50 mL). The organic layer was separated, washed once with saturated aqueous. NaHCO3 and once with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by radial chromatography on silica gel (elution with 20percent ethyl acetate in hexanes) to afford 470.0 mg (94percent) of the 9-[(2-pyridyl)methyl]-4-hydroxy-5-carbomethyoxy carbazole as a solid. 1H NMR (CDCl3) delta 10.37 (s, 1H), 8.61 (d, 1H, J=3.7 Hz), 8.01 (d, 1H, J=7.8 Hz), 7.63 (d, 1H, J=8.3 Hz), 7.47-7.39 (m, 3H), 7.19-7.14 (m, 1H), 6.94 (d, 1H, J=8.3 Hz), 6.84 (d, 1H, J=8.3 Hz), 6.59 (d, 1H, J=7.8 Hz), 5.66 (s, 2H), and 4.10 (s, 3H). IR (CHCl3, cm-1) 3200 (br), 1686, 1597, 1442, 1428, 1332, 1286, and 1268. MS (ES) m/e 333 (M+1). Elemental Analyses for C20H16N2O3: Calculated: C, 72.28; H, 4.85; N, 8.43. Found: C, 72.44; H, 4.79; N, 8.44.
  • 67
  • [ 247903-86-2 ]
  • [ 670-98-4 ]
  • 9-[(3-pyridyl)methyl]-4-hydroxy-5-carbomethyoxy carbazole [ No CAS ]
  • 9-[(pyridin-3-yl)methyl]-4-hydroxy-5-carbomethoxy carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
400 mg (92%) In 1,4-dioxane; mineral oil; B. 9-[(3-Pyridyl)methyl]-4-hydroxy-5-carbomethoxy Carbazole A solution of the 9-[(3-pyridyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one (456 mg, 1.31 mmol) in 3 mL of dioxane was treated with sodium hydride (128 mg; 3.20 mmol; 60percent dispersion in mineral oil) and the mixture stirred for 15 minutes. Methyl benzenesulfinate (0.32 mL; 2.45 mmol) was added dropwise and the reaction heated to 70° C. until tlc analysis indicated complete consumption of starting material (2 hours). The reaction was cooled and diluted with EtOAc (50 mL). The organic layer was separated, washed once with saturated aqueous. NaHCO3 and once with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by radial chromatography on silica gel (elution with 20percent then 30percent then 50percent then 75percent ethyl acetate in hexanes) to afford 400 mg (92percent) of the 9-[(3-pyridyl)methyl]-4-hydroxy-5-carbomethyoxy carbazole as a yellow solid. 1H NMR (DMSO-d6) delta 10.20 (s, 1H), 8.46 (d, 1H, J=2.0 Hz), 8.39 (d, 1H, J=4.9 Hz), 7.73 (d, 1H, J=8.3 Hz), 7.43-7.37 (m, 2H), 7.28-7.21 (m, 2H), 7.15-7.08 (m, 2H), 6.56 (d, 1H, J=7.8 Hz), 5.67 (s, 2H), and 3.80 (s, 3H). IR (KBr, cm-1) 1722, 1585, 1459, 1431, 1331, 1321, 1292, 1278, 1136, 781 and 763. MS (ES) m/e 333 (M+1). Elemental Analyses for C20H16N2O3: Calculated: C, 72.28; H, 4.85; N, 8.43. Found: C, 72.37; H, 4.67; N, 8.71.
  • 68
  • C5H5Ru((C6H5)3P)(CO)S(O)OCH3(C6H5)(1+)*BF4(1-)=C5H5Ru((C6H5)3P)(CO)S(O)OCH3(C6H5)BF4 [ No CAS ]
  • [ 75-05-8 ]
  • acetonitrile(carbonyl)(cyclopentadienyl)(triphenylphosphane) ruthenium tetrafluoroborate [ No CAS ]
  • [ 670-98-4 ]
  • 70
  • [ 1027775-22-9 ]
  • [ 670-98-4 ]
  • [ 1027776-11-9 ]
YieldReaction ConditionsOperation in experiment
With potassium hydride; In tetrahydrofuran; for 16h; To potassium hydride (35 weight percent in oil, washed with heptane (x3), 3.01 g, 26.3 mmol), in THF (20 mL) was added a solution of (3S,7aS)-7a-cyclopropyl-3-phenyltetrahydropyrrolo[2,l- b]oxazol-5(6H)-one (preparation No.23) (2.56 g, 10.5 mmol) in THF (20 mL) dropwise via an addition funnel. A solution of <strong>[670-98-4]methyl benzenesulfinate</strong> (1.97 g, 12.6 mmol) in THF (20 mL) was then added dropwise via an addition funnel. The reaction mixture was stirred at ambient temperature for about 16 hours. The reaction was quenched by the addition of water (4.2 mL). The mixture was concentrated and the residue was partitioned between 0.5 M H3PO4 (100 mL) and DCM (200 mL). The layers were separated and the aqueous layer was extracted with DCM (3 x 100 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered <n="133"/>and concentrated to yield a light brown solid. Toluene (83 mL) was added followed by solid Na2CC^ (10.35 g). The reaction mixture was refluxed for about 16 hours and then filtered and concentrated in vacuo. The residue was purified on a Biotage silica gel column eluting with heptane/EtOAc (4: 1). A second purification on silica gel eluting DCM/EtOAc (1:0 to 4: 1) afforded (3S,7aR)-7a-cyclopropyl-3-phenyl-2,3-dihydropyrrolo[2,l-b]oxazol-5(7aH)-one (1.82 g, 7.57 mmol). 1H NMR (CDCl3-**) delta 7.34 (m, 4H), 7.28 (m, IH), 7.11 (d, IH), 6.08 (d, IH), 5.06 (t, IH), 4.69 (t, IH), 4.43 (dd, IH), 1.14 (m, IH), 0.45 (m, 2H), 0.32 (m, IH), 0.21 (m, IH).
  • 71
  • [ 670-98-4 ]
  • [ 154479-61-5 ]
  • [ 865088-39-7 ]
YieldReaction ConditionsOperation in experiment
To a cooled (-20° C.) solution of 1-(4-fluorobenzyl)piperidine (17 g, 82 mmol) in anhydrous THF (200 mL) was added LiHMDS (1.0M in THF, 180 mL, 180 mmol) over a period of 15 min. The reaction mixture was stirred for 30 min at -20° C., then <strong>[670-98-4]methyl phenylsulfinate</strong> (15 g, 98 mmol) was added over a period of 5 min. After being stirred at -20° C. for 1 hour, the reaction was quenched by the addition of water (100 mL). EtOAc (200 mL) was added and the organic layer was separated and washed with water (3.x.100 mL) and brine. The organic layer was dried over Mg2SO4, filtered, concentrated under vacuum. The crude product was used without purification in the next step.
  • 72
  • [ 123-75-1 ]
  • [ 670-98-4 ]
  • [ 182356-71-4 ]
YieldReaction ConditionsOperation in experiment
at 35 - 40℃; for 2h;Sonication; Neat (no solvent); General procedure: A mixture of methyl sulfinate (1 mmol) and amine (1.5 mmol) was sonicated for 2-5 h. The reaction was monitored by TLC. The volatiles were evaporated under vacuum and the residue containing the sulfinamide was ready to use in the next step. To a solution of crude sulfinamide in CH2Cl2 (6 mL), commercial m-CPBA (1.5 equiv) was slowly added (about 15 min) at room temperature. When the reaction was completed (0.5-1 h), 40percent aqueous sodium bisulfite (5 mL) was added and the mixture was stirred for 5 min. The solution was extracted with CH2Cl2 (3.x.10 mL), the organic phase was washed with saturated NaHCO3 (2.x.30 mL), dried (Na2SO4), and concentrated. The corresponding sulfonamide was obtained pure in most of the cases. Otherwise, it was purified by column chromatography.
  • 73
  • [ 110-91-8 ]
  • [ 670-98-4 ]
  • [ 16066-32-3 ]
  • 74
  • [ 513-49-5 ]
  • [ 670-98-4 ]
  • (SS/RS)-[(S)-sec-butyl]benzenesulfinamide [ No CAS ]
  • 75
  • [ 670-98-4 ]
  • [ 16066-31-2 ]
YieldReaction ConditionsOperation in experiment
90% To a solution of <strong>[670-98-4]methyl benzenesulfinate</strong> 2 (4.48 g, 28.7 mmol) in anhydrous THF (60 mL), lithium bis(trimethylsilyl)amide (43 mL, 43 mmol) was added dropwise over 10 min at -78 C. The mixture was stirred for 10 min at -78 C and 1.5 h at room temperature. Then a saturated sol of NH4Cl (100 mL) was added and the mixture stirred overnight at room temperature. The reaction mixture was diluted by addition of ethyl acetate, the organic layer was separated and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The product was recrystallized from hexane/ethyl acetate 2:1. Benzenesulfinamide 3 (3.66 g, 90%) was isolated as colorless crystals. MS (ES+), m/z: 141.9 [(M+H)+]. 1H NMR (500 MHz, DMSO-d6) delta ppm 6.25 (s, 2H), 7.45-7.60 (m, 3H), 7.60-7.72 (m, 2H). 13C NMR (125 MHz, DMSO-d6) delta ppm 125.3, 128.6, 130.2, 148.1. Data in accordance with literature values.28
90% To a solution of <strong>[670-98-4]methyl benzenesulfinate</strong> (0.058 mol, 9.1 g) in THF (150 mL) at - 78 C, a 1M solution of LHMDS (0.088 mol) in THF was added. The temperature was warmed to rt and the reaction mixture was stirred for 2 h. When the reaction was finished (followed by TLC), the reaction was quenched with 50 mL a saturated NH4Cl solution and stirred for 1 h. The reaction was extracted with AcOEt (2 x 100 mL), dried over anhydrous Na2SO4, and solvent was removed under vacuum. The brown solid was crystallized from hexane, obtaining 7.36g of 3e as a white solid ( 90% yield). 1H NMR (400 MHz, CDCl3) delta 8.13 - 7.62 (m, 2H), 7.64 - 7.40 (m, 3H), 4.42 (s, 2H). 13C NMR (101 MHz, CDCl3) delta 131.12, 128.93, 125.42. HRMS (ESI): C6H7NOS Neutral mass: 141.02483, Observed neutral mass: 141.0250, Observed ([M+Na])+ : 164.0138.
65% General procedure: To a solution of the <strong>[670-98-4]methyl benzenesulfinate</strong> (0.015 mol) in THF (30 mL) at -78 C, 1 M solution of LiHMDS (0.023 mol) in THF was added. The temperature was warmed to r.t. and the reaction mixture was stirred for 2 h. When the reaction was finished (followed by TLC), the reaction was quenched with 50 mL a saturated NH4Cl solution and stirred for 1 h. The reaction was extracted with AcOEt (2 x 100 mL), dried over anhydrous Na2SO4, and solvent was removed under vacuum. The residue was crystallized from hexane. Benzenesulfinamide (2a). Benzenesulfinamide (2a) was prepared from <strong>[670-98-4]methyl benzenesulfinate</strong>1 according to the general method affording 1.37 g of 4a (65%) as a white solid, Mp: 103 C. 1H NMR (400 MHz, CDCl3) delta 8.13 - 7.62 (m, 2H), 7.64 - 7.40 (m, 3H), 4.42 (s, 2H). 13C NMR (101 MHz, CDCl3) delta 131.12, 128.93, 125.42. HRMS (ESI): C6H7NOS Neutral mass: 141.02483, Observed neutral mass: 141.0250, Observed ([M+Na])+: 164.0138.
  • 76
  • [ 670-98-4 ]
  • [ 2577-90-4 ]
  • [ 137451-39-9 ]
  • 77
  • [ 670-98-4 ]
  • [ 3886-69-9 ]
  • C14H15NOS [ No CAS ]
  • 78
  • [ 670-98-4 ]
  • [ 108-91-8 ]
  • [ 35810-04-9 ]
  • 79
  • [ 670-98-4 ]
  • [ 109-89-7 ]
  • [ 112425-44-2 ]
  • 81
  • [ 670-98-4 ]
  • [ 107-11-9 ]
  • [ 1017238-68-4 ]
  • 82
  • [ 670-98-4 ]
  • [ 1088435-25-9 ]
  • C24H27NO3S [ No CAS ]
  • 83
  • [ 670-98-4 ]
  • [ 972-46-3 ]
  • [ 1150561-23-1 ]
YieldReaction ConditionsOperation in experiment
Step 2: Androsta-4,15-diene-3,17-dioneA solution of 20.28 g (0.172 moles) of potassium ter-butylate 95percent in600 ml of tetrahydrofuran, blanketed with nitrogen, is treated with 30 g (0.095 moles) of 3-ethoxy-androsta-3,5-diene-17-one at 20-300C, whereby a yellow-orange solution is formed. The mixture is stirred at 20-250C for ten minutes, then treated with 26.34 g (0.165 moles) of 98percent <strong>[670-98-4]methyl benzenesulfinate</strong>: temperature rises up to 35°C. After stirring at 0-300C for 30 minutes, a dark solution is obtained. The solution is then poured into a mixture of 600 ml of water and 60 ml of 35percent hydrochloric acid, in about 20 minutes, keeping temperature between 10° and 200C. Stirring is maintained at such temperature for additional 2.5 hours.600 ml of xylene are added, and after stirring for 15 minutes, phases are separated. The lower aqueous phase is washed with 300 ml of xylene, and, after stirring for 15 minutes, phases are separated. The organic phases are collected and treated with 50.4 g (0.475 moles) of sodium carbonate; the mixture is heated under nitrogen atmosphere to distil off the solvent until an internal temperature of 1300C is reached (710 ml are distilled off), then maintained at reflux for 4 hours, and finally cooled at 20°/30°C. Solids are removed by filtration, washed with 2 x 120 ml of xylene; the solution is concentrated under vacuum until an oily residue is obtained (45.45 g).After chromatographic separation, 16 g of androsta-4,15-diene-3,17- dione are obtained. <n="8"/>Molar yield: 59.2percent.Analysis: 1H-NMR (CDCl3): delta (ppm) 1.12 (s, 3H, CH3); 1.26 (s, 3H, CH3); 5.77 (s, IH, CH); 6.01 (m, IH, CH); 7.52 (d, IH, CH).
  • 84
  • [ 670-98-4 ]
  • [ 20808-12-2 ]
  • [ 1151549-59-5 ]
  • 85
  • [ 670-98-4 ]
  • C25H45NO2Si [ No CAS ]
  • C31H49NO3SSi [ No CAS ]
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