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[ CAS No. 5402-55-1 ] {[proInfo.proName]}

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Chemical Structure| 5402-55-1
Chemical Structure| 5402-55-1
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Product Details of [ 5402-55-1 ]

CAS No. :5402-55-1 MDL No. :MFCD00005462
Formula : C6H8OS Boiling Point : -
Linear Structure Formula :- InChI Key :VMJOFTHFJMLIKL-UHFFFAOYSA-N
M.W : 128.19 Pubchem ID :79400
Synonyms :

Calculated chemistry of [ 5402-55-1 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.25
TPSA : 48.47 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 1.28
Log Po/w (MLOGP) : 0.84
Log Po/w (SILICOS-IT) : 2.67
Consensus Log Po/w : 1.56

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.77
Solubility : 2.2 mg/ml ; 0.0172 mol/l
Class : Very soluble
Log S (Ali) : -1.89
Solubility : 1.66 mg/ml ; 0.013 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.86
Solubility : 1.77 mg/ml ; 0.0138 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 5402-55-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5402-55-1 ]

* 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.

  • Upstream synthesis route of [ 5402-55-1 ]
  • Downstream synthetic route of [ 5402-55-1 ]

[ 5402-55-1 ] Synthesis Path-Upstream   1~25

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Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 5, p. 3116 - 3124
  • 2
  • [ 1918-77-0 ]
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YieldReaction ConditionsOperation in experiment
72% With strain of the zygomycete fungus S. racemosum MUT 770 In dimethyl sulfoxide for 72 h; Enzymatic reaction 2.3. Biotransformation experimentsFungal strains were pre-grown in Petri dishes containing maltextract solid medium (MEA: 20 g L−1 glucose, 20 g L−1 malt extract,20 g L−1 agar, 2 g L−1 peptone) from which the inoculum for liquidcultures was set up. The fungus was inoculated as conidia suspen-sion (1 106 conidia/mL) in 50 mL asks containing 40 mL of maltextract liquid medium. Flasks were incubated at 25 C and weremaintained under agitation (110 rpm).After 2 days of pre-growth, a 500 mM solution of the substratein DMSO was added, to a starting substrate concentration (c0) of1–5 mM. For each substrate, three biological replicates were run.The experiment was run for 3 days after the addition of the sub-strates, during which time 1 mL samples were taken, at speciedintervals (usually 24, 48, and 72 h). Each sample was extractedwith EtOAc (500 L), the organic phase was dried over anhydrousNa2SO4 and analysed by means of GC/MS. In some cases (see Section2.4) the isolation of the reduced product has been carried out.For each set of biotransformations, one ask was used to mea-sure the initial biomass and pH before the addition of the substrate.These parameters were also evaluated at the end of the experimentfor all the asks. The liquid media was separated from the biomassby ltration and was used for pH measurement while the myceliawere dried at 60 C for 24 h to measure the biomass dry weight. 2-(Thiophen-2-yl)ethanol: from 2-(thiophen-2-yl)acetic acid(3.7 mg, 72percent) and from methyl 2-(thiophen-2-yl)acetate (24.6 mg,96percent). 1H NMR (400 MHz, CDCl3, TMS): = 7.20 (m, 1H, heteroaro-matic hydrogen), 6.99 (m, 1H, heteroaromatic hydrogen), 6.90 (m,1H, heteroaromatic hydrogen), 3.85 (t, 2H, J = 6.2 Hz, CH2OH), 3.02(t, 2H, J = 6.2 Hz, CH2CH2OH). 13C NMR (100 MHz, CDCl3, TMS): = 140.5, 127.0, 125.8, 124.0, 63.4, 33.3. GC/MS: tR = 9.47 min, m/z128 (M+, 30), 110 (5), 97 (100)
66.5%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;
Stage #2: With water; sodium chloride In tetrahydrofuran at 0℃;
Step 9
2-(Thiophen-2-yl)ethanol:
At about 0° C., a solution of thiophen-2-yl-acetic acid (1.0 g; 7.03 mmol) in tetrahydrofuran (10 mL) was added dropwise to a suspension of lithium aluminum hydride (0.534 g; 14.05 mmol) in dry tetrahydrofuran (10 mL).
The mixture was stirred at ambient temperature for about 4 hours, and then cooled to about 0° C.
After adding a cold saturated sodium chloride solution (1 mL), the mixture was filtered, and the inorganic salts were washed with tetrahydrofuran and ethyl acetate.
The filtrate and washings were combined and concentrated in vacuo to give the title compound as brown oil (0.600 g; 66.5percent).
1H NMR (400 MHz, CDCl3) δ 1.60 (br, exchangeable with D2O, 1H), 3.08 (t, J=6.2 Hz, 2H), 3.85 (t, J=6.2 Hz, 2H), 6.87-6.88 (m, 1H), 6.95-6.97 (m, 1H), 7.16-7.25 (m, 1H). IR (film) υ 3345, 3105, 2211, 2126, 2090, 1792, 1433, 1138, 972, 737, 699 cm-1 MS: 129 (M+1).
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 3, p. 346 - 357
[2] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 85, p. 10514 - 10516,3
[3] European Journal of Organic Chemistry, 2011, # 17, p. 3178 - 3183
[4] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 116, p. 83 - 88
[5] Patent: US2010/16365, 2010, A1, . Location in patent: Page/Page column 26
[6] Synthesis, 2011, # 18, p. 2935 - 2940
  • 3
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YieldReaction ConditionsOperation in experiment
96% With strain of the zygomycete fungus S. racemosum MUT 770 In dimethyl sulfoxide for 72 h; Enzymatic reaction 2.3. Biotransformation experimentsFungal strains were pre-grown in Petri dishes containing maltextract solid medium (MEA: 20 g L−1 glucose, 20 g L−1 malt extract,20 g L−1 agar, 2 g L−1 peptone) from which the inoculum for liquidcultures was set up. The fungus was inoculated as conidia suspen-sion (1 106 conidia/mL) in 50 mL asks containing 40 mL of maltextract liquid medium. Flasks were incubated at 25 C and weremaintained under agitation (110 rpm).After 2 days of pre-growth, a 500 mM solution of the substratein DMSO was added, to a starting substrate concentration (c0) of1–5 mM. For each substrate, three biological replicates were run.The experiment was run for 3 days after the addition of the sub-strates, during which time 1 mL samples were taken, at speciedintervals (usually 24, 48, and 72 h). Each sample was extractedwith EtOAc (500 L), the organic phase was dried over anhydrousNa2SO4 and analysed by means of GC/MS. In some cases (see Section2.4) the isolation of the reduced product has been carried out.For each set of biotransformations, one ask was used to mea-sure the initial biomass and pH before the addition of the substrate.These parameters were also evaluated at the end of the experimentfor all the asks. The liquid media was separated from the biomassby ltration and was used for pH measurement while the myceliawere dried at 60 C for 24 h to measure the biomass dry weight. 2-(Thiophen-2-yl)ethanol: from 2-(thiophen-2-yl)acetic acid(3.7 mg, 72percent) and from methyl 2-(thiophen-2-yl)acetate (24.6 mg,96percent). 1H NMR (400 MHz, CDCl3, TMS): = 7.20 (m, 1H, heteroaro-matic hydrogen), 6.99 (m, 1H, heteroaromatic hydrogen), 6.90 (m,1H, heteroaromatic hydrogen), 3.85 (t, 2H, J = 6.2 Hz, CH2OH), 3.02(t, 2H, J = 6.2 Hz, CH2CH2OH). 13C NMR (100 MHz, CDCl3, TMS): = 140.5, 127.0, 125.8, 124.0, 63.4, 33.3. GC/MS: tR = 9.47 min, m/z128 (M+, 30), 110 (5), 97 (100)
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 7, p. 2785 - 2788
[2] Synthetic Communications, 2005, vol. 35, # 24, p. 3187 - 3190
[3] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 116, p. 83 - 88
[4] Advanced Synthesis and Catalysis, 2012, vol. 354, # 10, p. 1879 - 1884
[5] Synthesis, 2011, # 18, p. 2935 - 2940
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Reference: [1] Catalysis Science and Technology, 2018, vol. 8, # 14, p. 3504 - 3512
[2] Synthetic Communications, 2005, vol. 35, # 24, p. 3187 - 3190
[3] Journal of Organic Chemistry, 1994, vol. 59, # 15, p. 4323 - 4326
[4] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 9, p. 2730 - 2734
[5] Journal of the American Chemical Society, 1991, vol. 113, # 13, p. 5093 - 5095
[6] Journal of Organic Chemistry, 1992, vol. 57, # 14, p. 3751 - 3753
[7] Chemistry - A European Journal, 2011, vol. 17, # 27, p. 7414 - 7417
  • 5
  • [ 765-50-4 ]
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YieldReaction ConditionsOperation in experiment
45%
Stage #1: With chloro-trimethyl-silane; ethylene dibromide; zinc In tetrahydrofuran at 70℃; for 2 h; Schlenk technique; Inert atmosphere
Stage #2: at 70℃; for 6 h; Schlenk technique; Inert atmosphere
General procedure: Phenethyl alcohol (3a) A two neck Schlenk flask equipped with a magnetic stirring bar and septum was heated with heat gun (~400 °C) for 10 min under high vacuum. After cooling to room temperature, the flask was flushed with argon (3 times). Zn-dust (654 mg, 2.0 equiv, 10.0 mmol) was added followed by THF (20 mL). 1,2-Dibromoethane (5 molpercent) was added and the reaction mixture was heated until ebullition occurs. After cooling to rt, chlorotrimethylsilane (1 molpercent) was added and the mixture was heated again till ebullition occurs. The flask was again cooled to rt and benzyl chloride (633 mg, 5.0 mmol, 1 equiv) was added as a solution in THF (10 mL) and it was heated at 70 °C for 2 h and cooled to rt. Paraformaldehyde (450 mg, 3.0 equiv. 15.0 mmol) was slowly added at rt and the flask was again heated at 70 °C for 6 h. The solution was cooled to rt and saturated NH4Cl solution was added. The phases were separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was washed with water (20 mL), brine (10 mL) and then dried over Na2SO4. The solvents were evaporated under reduced pressure and the residue was purified by silica gel column chromatography using cyclohexane or cyclohexane/ethyl acetate as an eluent to obtain phenethyl alcohol (3a) (510 mg, 83percent) as a colourless liquid.
Reference: [1] Synthetic Communications, 2017, vol. 47, # 10, p. 968 - 974
  • 6
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YieldReaction ConditionsOperation in experiment
83%
Stage #1: With sodium; polyethylene; isoprene In tetrahydrofuran; toluene at -1 - 1℃; for 3.5 h;
Stage #2: at 19 - 21℃; for 2 h;
Stage #3: With water; ammonium chloride In tetrahydrofuran; toluene at 0 - 22℃; for 0.25 h; Cooling with ice-methanol bath
2-Ethyl-2-ethanol a) Preparation of the Sodium Suspension 53 g (61 ml) of toluene, 0.0265 g of polyethylene and 26.5 g (1.15 mol) of sodium cut into pieces are placed in a 250 ml round-bottomed flask under nitrogen, equipped with a stirrer and a condenser. The mixture is heated to 102° C. and then stirred for 0.5 hour. The suspension is then cooled to a temperature of between 20° C. and 25° C. b) Metallation of the Thiophene 145.4 g (133.7 ml; 1.731 mol) of thiophene are placed in a 1 l jacketed reactor under nitrogen, equipped with a dropping funnel and cooled with chilled dichloromethane. The mixture is cooled to 0° C..+-.1° C. with stirring. The sodium suspension is then diluted, followed by addition to the thiophene. While keeping the temperature at 0° C..+-.1° C., this thiophene/sodium suspension is then added to a mixture of 51.8 g (76 ml; 0.762 mol) of isoprene in 166 g (187 ml; 2.3 mol) of tetrahydrofuran maintained at 0° C..+-.1° C. Under these conditions, the introduction time is about 1.5 h. The reaction is then maintained at 0° C..+-.1° C. for 2 hours. c) Oxyethylenation 55.8 g (1.270 mol) of ethylene oxide are added to the mixture obtained in paragraph b) above, via a dip tube, while maintaining the temperature at 20° C..+-.1° C. The duration of this addition is about 1.5 h. The suspension is then stirred for 0.5 h at 20° C..+-.1° C. d) Hydrolysis 300 ml of water and 74 g of ammonium chloride are placed in a 2 l reactor equipped with a cooling and stirring system. This solution is cooled to a temperature of between -5° C. and 0° C. and the reaction mixture obtained in paragraph c) is then transferred, by nitrogen pressure, over 10 to 15 minutes, onto the ammonium chloride solution. Under these conditions and with a cooling bath containing ice and methanol, the temperature at the end of hydrolysis is 20° C. The mixture is stirred for 15 minutes at 20° C..+-.2° C., the phases are separated by settling for 15 minutes and the (upper) organic phase is washed 3 times at 20° C..+-.2° C. with 200 ml of water. The combined aqueous phases are extracted 3 times at 20° C..+-.2° C. using 100 ml (86 g) of toluene. The organic phases are pooled and the toluene solution is concentrated under vacuum (50° C.; 15 mmHg). In this way, 133 g of crude 2-thienyl-2-ethanol are obtained. Yield: 83percent.
83%
Stage #1: With cis-Octadecenoic acid; sodium; isopropenylbenzene In tetrahydrofuran; toluene at -1 - 1℃; for 3.5 h;
Stage #2: at 19 - 21℃; for 2 h;
Stage #3: With water In tetrahydrofuran; toluene at 0 - 20℃; for 0.166667 - 0.25 h; Cooling with ice-methanol bath
2-Ethyl-2-ethanol a) Preparation of the Sodium Suspension 69 g (80 ml) of toluene, 0.0230 g of oleic acid and 23 g (1 mol) of sodium cut into pieces are placed in a 250 ml round-bottomed flask under nitrogen, equipped with a stirrer and a condenser. The mixture is heated to 102° C. and then stirred for 0.5 hour. The suspension is then cooled to a temperature of between 20° C. and 25° C. b) Metallation of the Thiophene 126 g (1.5 mol ) of thiophene are placed in a 1 l jacketed reactor under nitrogen, equipped with a dropping funnel and cooled with chilled isopropanol. The mixture is cooled to 0° C..+-.1° C. with stirring. The sodium suspension is then diluted, followed by addition to the thiophene. While keeping the temperature at 0° C..+-.1° C., this thiophene/sodium suspension (76 ml; 0.762 mol) is then added to a mixture of 79 g (0.670 mol) of α-methylstyrene in 144 g (2 mol) of tetrahydrofuran maintained at 0° C..+-.1° C. Under these conditions, the introduction time is about 1.5 h. The reaction medium is then maintained at 0° C..+-.1° C. for 2 hours. c) Oxyethylenation 48 g (1.1 mol) of ethylene oxide are added to the mixture obtained in paragraph b) above, via a dip tube, while maintaining the temperature at 20° C..+-.1° C. The duration of this addition is about 1.5 h. The suspension is then stirred for 0.5 h at 20° C..+-.1° C. d) Hydrolysis 230 ml of water are placed in a 2 l reactor equipped with a cooling and stirring system. This solution is cooled to a temperature of between 0° C. and 5° C. and the reaction medium obtained in paragraph c) is then transferred into the water, over 10 to 15 minutes. Under these conditions and with a cooling bath containing ice and methanol, the temperature at the end of hydrolysis is in the region of 20° C. The phases are separated by settling and the upper organic phase is concentrated under vacuum (50° C.; 15 mmHg). In this manner, 239 g of crude 2-thienyl-2-ethanol are obtained. Yield: 83percent.
83%
Stage #1: With cis-Octadecenoic acid; sodium; 2,3-dimethyl-buta-1,3-diene In tetrahydrofuran; toluene at -1 - 1℃; for 2 h;
Stage #2: at 20℃; for 0.333333 h;
Stage #3: With water In tetrahydrofuran; toluene at 0 - 13℃; for 0.5 h;
Preparation of 2-thienyl-2-ethanol a) Preparation of the Sodium Suspension 84.3 g of dry toluene, 0.32 ml of oleic acid and 28.1 g (1.2217 mol) of sodium cut into pieces are placed into a 250 ml round-bottomed flask under nitrogen, equipped with a stirrer and a condenser. The mixture is heated to 102° C. and then stirred for 0.5 h. The suspension is then cooled to a temperature in the region of 25° C. b) Metallation of the Thiophene 154.2 g (1.5 equivalents) of thiophene are placed in a jacketed 1 l reactor under a nitrogen atmosphere, equipped with a dropping funnel and cooled. The flask is cooled to 0° C. with stirring and the sodium suspension is added to the thiophene. 67.2 g (0.67 equivalent) of 2,3-dimethyl-1,3-butadiene are added to 176 g (2 equivalents) of tetrahydrofuran, while keeping the temperature at 0° C..+-.1° C. The reaction medium is then maintained at 0° C. for 2 hours. c) Oxyethylenation 59.2 g of ethylene oxide are added, via a dip tube, to the mixture obtained in paragraph b) above, while keeping the temperature below or equal to 20° C. The reaction medium is then left for 20 minutes at 20° C. with stirring. d) Hydrolysis The suspension obtained in paragraph c) is transferred, over 5 minutes and under a nitrogen pressure, into a 2 liter reactor containing 281 g of ice under nitrogen. The temperature of the medium at the end of introduction is 13° C. The mixture is stirred for 30 minutes and the phases are separated by settling. The organic phase is extracted with 100 ml of toluene, stirred for 30 minutes and the phases are separated by settling. The organic phase is then concentrated under vacuum. In this way, 145.6 g of 2-thienyl-2-ethanol are obtained. Yield: 83percent.
Reference: [1] Patent: US6639083, 2003, B1, . Location in patent: Page/Page column 3-4
[2] Patent: US6639083, 2003, B1, . Location in patent: Page/Page column 4-5
[3] Patent: US6639083, 2003, B1, . Location in patent: Page/Page column 5
[4] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 22, p. 3465 - 3470
[5] Zhurnal Obshchei Khimii, 1955, vol. 25, p. 1373,1374; engl. Ausg. S. 1321, 1322
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Reference: [1] Synthesis, 2008, # 11, p. 1793 - 1797
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Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 32, p. 4820 - 4826
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Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 7009 - 7019
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Reference: [1] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 85, p. 10514 - 10516,3
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Reference: [1] Bulletin de la Societe Chimique de France, 1948, p. 1083,1085
[2] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 997,1001; engl. Ausg. S. 1079, 1082
[3] Journal of the American Chemical Society, 1953, vol. 75, p. 6329
[4] Journal of the Chemical Society, 1957, p. 4967,4969
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Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 1646
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Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 477,479
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Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 7009 - 7019
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Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 7009 - 7019
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Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7884 - 7890
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Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 75 - 79
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Reference: [1] Zhurnal Obshchei Khimii, 1955, vol. 25, p. 1373,1374; engl. Ausg. S. 1321, 1322
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  • [ 620-02-0 ]
  • [ 5402-55-1 ]
  • [ 1192-62-7 ]
  • [ 2527-76-6 ]
  • [ 1072-83-9 ]
  • [ 28588-74-1 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 5, p. 3116 - 3124
  • 20
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YieldReaction ConditionsOperation in experiment
85% With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; water; acetonitrile at 35℃; for 6 h; Green chemistry In the reactor were added 2-thiophene ethanol 10g, TEMPO 0.4g, acetonitrile, 200mL, pH = phosphate buffer 100mL (0.6mol.L 6.5 of-1), uniformly stirred, the reactor temperature was raised to 35 ;Was then slowly added dropwise to the reactor an aqueous solution of NaClO (16wtpercent) 80g, 2h addition was complete, the reaction was continued for 4h, was added 2mol.L-1sodium sulfite solution, until the reactor is completely neutralized NaClO (starch iodide test paper); Plus 2mol.L-1of NaOH solution was adjusted to a weakly alkaline, extracted with ethyl acetate and the catalyst was completely unreacted starting material and then using 4mol.L-1HCI solution was adjusted to pH 1, and extracted with ethyl acetate to give 2- The crude acid thiophene; The crude product was recrystallized from petroleum ether to give pure 2-thiophene acetic acid, the liquid detection purity of 99percent, the conversion rate of 2-thiophene ethanol of 100percent and the reaction selectivity was 95percent and yield was 85percent.
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8344 - 8347
[2] Patent: CN104725345, 2017, B, . Location in patent: Paragraph 0035-0069
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  • [ 98-59-9 ]
  • [ 40412-06-4 ]
YieldReaction ConditionsOperation in experiment
98% at 35℃; Cooling with ice (0.87 mol) of 2-thiopheneethanol and 184 g (0.97 mol) of p-toluenesulfonyl chloride were sequentially added to a 1 L three-necked flask, 98 g (0.97 mol) of triethylamine was dropwise added thereto under ice-water bath, And keep the temperature of the reaction liquid not higher than 20 DEG C, dropping finished, heating to 35 DEG C to continue stirring, respectively 24h, 27h sampling, TLC, until the reaction is complete, stop reaction, filtration, filter cake with appropriate amount of dichloromethane And the methylene chloride layer was dried with anhydrous sodium sulfate for 2 hours. The desiccant was filtered off and the desiccant was washed with a small amount of methylene chloride. The filtrate was decompressed in vacuo and the filtrate was evaporated under reduced pressure. Concentrated to constant weight to be brown oil, weighing 203g, yield 98percent,
96.37% With triethylamine In toluene at 5 - 30℃; for 20.8333 h; EXAMPLE 3
Preparation of 2-Thienylethyl Para-Toluenesulphonate (Formula VII) Using Toluene
400 liters of toluene and 163.2 kg of para-toluene sulfonyl chloride were charged into a clean and dry reactor followed by cooling to about 5° C. 100 kg of thiophene-2-ethanol was added at about 5° C. over about 20 minutes followed by addition of 130 kg of triethylamine over about 8 hours, 50 minutes.
The reaction mixture temperature was raised to about 30° C. followed by stirring for about 12 hours.
The reaction mass was filtered through a Nutsche filter and washed with 2*100 liters of toluene.
The reaction filtrate was transferred into another reactor followed by washing with 5*200 liters of water.
Organic and aqueous layers were separated and the organic layer was distilled completely at about below 70° C. under vacuum to afford 212 kg (yield: 96.37percent) of title compound.
Purity by GC: 95.59percent.
96.5% With triethylamine In dichloromethane at -5 - 20℃; for 2 h; 32.7 g (0.17 mol) of p-toluenesulfonyl chloride,40 ml of dichloromethane into the reaction flask, cooled to -5 ° C,20 g (0.16 mol)2-thiopheneethanol.28.4 g (0.28 mol) of triethylamine was slowly added dropwise and the temperature of the reaction solution was maintained at about 0 ° C.Plus Bi, incubated for 2h after the reaction was warmed to room temperature. 2-thiophene ethanol to be consumed until the raw materials, suction filtration,The solid was washed with a small amount of methylene chloride and the filtrate was washed with 50 ml of saturated sodium bicarbonate and dried over anhydrous sodium sulfate. Filtration, concentration of the filtrate, light brown solid precipitated out,Filtered, washed with a small amount of petroleum ether to white,That isP-toluenesulfonate-2-thiophene ethyl ester42.5 g, yield 96.5percent (HPLC purity 99percent)
95.5% With triethylamine In dichloromethane at 7.5 - 22.5℃; for 5 h; EXAMPLE 10
Preparation of 2-(2-Thiophene)Ethanol Tosylate (Formula VII) Using Dichloromethane
4 liters of dichloromethane was added into a reactor at a temperature of about 30° C., cooled to a temperature of about 7.5° C. to which was then added 1.784 kg of p-toluene sulphonyl chloride followed by 1 kg of thiophene-2-ethanol.
1.302 kg of triethylamine was added to the above reaction mass at a temperature of about 7.5° C. followed by slowly raising the temperature of the reaction mass to 22.5° C. for about 5 hours.
The obtained reaction mass was filtered through a pressure Nutsche filter, washed with methylene chloride (2*1 liter) and the mother liquor was collected and transferred into another reactor.
The organic layer was washed with water (5*2 liters).
The organic layer thus obtained was subjected to distillation at a temperature below 70° C. using hot water circulation.
The obtained residue was then cooled to about 30° C. to afford 2.1 kg (yield: 95.5percent) of title compound.
93.6% With triethylamine In toluene at 45℃; for 4 h; Example 1 0.2. Conversion of (S)-1 ,2,3,4-tetrahydro-5-hvdroxy-N-propyl- naphthalen-2-ammonium hydrobromide (VIII) into hydrochloride salt of rotigotine; 10.2.1. Preparation of 2-(2-Thienyl)ethyl-4-toluene sulfonate; 4-toluenesulfonyl chloride (162 g), toluene (363.3 g) and 2-(2-Thienyl)ethanol (104 g) are combined. Triethylamine (93 g) is added maintaining the temperature lower than 45° C. After 4hrs, the mixture is washed with aqueous phosphoric acid, aqueous sodium hydroxide and then water. The organic phase is distilled off under vacuum. Isopropanol (314 g) and heptanes (365.9 g) are added. The batch is crystallized by cooling and isolated at -15° C. The crystals are filtered and washed with heptanes (175 mL). The crystals are then dried under vacuum at room temperature until a melting point of > 30° C is obtained.Yield ( 214 g): 93.6 percentHPLC analyses confirmed purity >99percent and 100 percent assay in comparison to a reference standard.
93.6% With triethylamine In toluene at 45℃; for 4 h; 4-toluenesulfonyl chloride (162 g), toluene (363.3 g) and 2-(2-Thienyl)ethanol (104 g) are combined. Triethylamine (93 g) is added maintaining the temperature lower than 45° C. After 4 hrs, the mixture is washed with aqueous phosphoric acid, aqueous sodium hydroxide and then water. The organic phase is distilled off under vacuum. Isopropanol (314 g) and heptanes (365.9 g) are added. The batch is crystallized by cooling and isolated at −15° C. The crystals are filtered and washed with heptanes (175 mL). The crystals are then dried under vacuum at room temperature until a melting point of 30° C. is obtained. [0255] Yield (214 g): 93.6percent
90% With silica gel In dichloromethane for 2 h; Reflux The 12.8g (0.1mol) 2- (2- thienyl) ethanol, 1000mL of dichloromethane, 21.0g (0.12mol) of p-toluenesulfonic acid chloride and 10.0g of silica gel into the reaction flask, the reaction was refluxed for 2h, cooled, filtered to remove silica gel.The reaction mixture was washed successively with distilled water, saturated sodium carbonate solution, brine, then the methylene chloride solvent was removed by distillation under reduced pressure, to give 26.0g of p-toluenesulfonic acid Preparation of 2- (2-thienyl) ethyl ester, 90percent yield .

Reference: [1] Patent: CN103467486, 2016, B, . Location in patent: Paragraph 0094-0096
[2] Patent: US2007/225320, 2007, A1, . Location in patent: Page/Page column 5
[3] Patent: CN107056801, 2017, A, . Location in patent: Paragraph 0016
[4] Patent: US2007/225320, 2007, A1, . Location in patent: Page/Page column 7
[5] Patent: WO2011/161255, 2011, A2, . Location in patent: Page/Page column 36
[6] Patent: US2013/102794, 2013, A1, . Location in patent: Paragraph 0254-0255
[7] Patent: CN104177328, 2016, B, . Location in patent: Paragraph 0015; 0016
[8] Angewandte Chemie - International Edition, 2014, vol. 53, # 7, p. 1809 - 1813[9] Angew. Chem., 2014, vol. 126, # 07, p. 1840 - 1844,5
[10] Journal of Heterocyclic Chemistry, 1989, vol. 26, # 3, p. 677 - 686
[11] Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1527 - 1529
[12] Patent: US4399140, 1983, A,
[13] Patent: WO2010/73124, 2010, A2, . Location in patent: Page/Page column 26
[14] Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 528 - 532
[15] Patent: US2011/313176, 2011, A1, . Location in patent: Page/Page column 11
[16] Patent: CN105503902, 2016, A, . Location in patent: Paragraph 0017
[17] Patent: CN105399753, 2016, A, . Location in patent: Paragraph 0017
[18] Patent: CN105601645, 2016, A, . Location in patent: Paragraph 0018
[19] Patent: CN105541862, 2016, A, . Location in patent: Paragraph 0015; 0017
[20] Patent: CN105461735, 2016, A, . Location in patent: Paragraph 0018
[21] Patent: CN108707156, 2018, A, . Location in patent: Paragraph 0006; 0008
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  • [ 5402-55-1 ]
  • [ 104-15-4 ]
  • [ 40412-06-4 ]
YieldReaction ConditionsOperation in experiment
78% With ferric nitrate In 1,2-dichloro-ethaneReflux 12.8 g (0.1 mol) of 2-thiopheneethanol,20.0 g (0.12 mol) of p-toluenesulfonic acid,20.2 g (0.05 mol) of ferric nitrate,100 ml of 1,2-dichloroethane into the reaction flask,Reflux reaction to 2 - thiophene ethanol consumption is completed,filter,The filtrate was washed three times with water,concentrate,The solvent was distilled off under reduced pressure,2-thiophene ethyl p-toluenesulfonate 22g,Yield 78percent.
Reference: [1] Tetrahedron Asymmetry, 2010, vol. 21, # 17, p. 2136 - 2141
[2] Patent: CN106866617, 2017, A, . Location in patent: Paragraph 0011; 0012
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  • [ 5402-55-1 ]
  • [ 53885-35-1 ]
Reference: [1] Patent: CN105503902, 2016, A,
[2] Patent: CN105399753, 2016, A,
[3] Patent: CN105601645, 2016, A,
[4] Patent: CN105541862, 2016, A,
[5] Patent: CN105461735, 2016, A,
  • 24
  • [ 5402-55-1 ]
  • [ 28783-41-7 ]
Reference: [1] Patent: CN107056801, 2017, A,
  • 25
  • [ 5402-55-1 ]
  • [ 160744-13-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 16, p. 2502 - 2524
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