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Chemistry
Heterocyclic Building Blocks
Tetrahydropyrans
2-(2-Chloroethoxy)tetrahydro-2H-pyran
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Tetrahydropyrans
Chlorides Ethers Aliphatic Heterocycles

[ CAS No. 5631-96-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Quality Control of [ 5631-96-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 5631-96-9 ]

Product Details of [ 5631-96-9 ]

CAS No. :5631-96-9 MDL No. :MFCD00142761
Formula : C7H13ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZVVQFPGYDBUGQB-UHFFFAOYSA-N
M.W : 164.63 Pubchem ID :254951
Synonyms :

Calculated chemistry of [ 5631-96-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.61
TPSA : 18.46 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) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.38
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 1.77
Log Po/w (MLOGP) : 1.31
Log Po/w (SILICOS-IT) : 2.19
Consensus Log Po/w : 1.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.63
Solubility : 3.89 mg/ml ; 0.0236 mol/l
Class : Very soluble
Log S (Ali) : -1.53
Solubility : 4.9 mg/ml ; 0.0297 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.94
Solubility : 1.91 mg/ml ; 0.0116 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.38

Safety of [ 5631-96-9 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P280-P403+P235-P501 UN#:1993
Hazard Statements:H225 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 5631-96-9 ]

* 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 [ 5631-96-9 ]

[ 5631-96-9 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 5631-96-9 ]
  • [ 20654-44-8 ]
  • [ 6570-87-2 ]
Reference： [1]Synthesis,1976,p. 391 - 393
  • 2
  • [ 5631-96-9 ]
  • [ 59346-64-4 ]
  • [ 38514-15-7 ]
Reference： [1]Synthesis,1976,p. 391 - 393
  • 3
  • [ 5631-96-9 ]
  • [ 109652-06-4 ]
  • [ 25245-03-8 ]
Reference： [1]Arzneimittel-Forschung/Drug Research,1969,vol. 19,p. 1193 - 1198
  • 4
  • [ 5631-96-9 ]
  • [ 766-05-2 ]
  • [ 4442-79-9 ]
Reference： [1]Synthesis,1976,p. 391 - 393
  • 5
  • [ 5631-96-9 ]
  • [ 100-45-8 ]
  • [ 60564-98-9 ]
Reference： [1]Synthesis,1976,p. 391 - 393
  • 6
  • [ 5631-96-9 ]
  • [ 100-45-8 ]
  • [ 18240-10-3 ]
Reference： [1]Synthesis,1976,p. 391 - 393
  • 7
  • [ 110-87-2 ]
  • [ 107-07-3 ]
  • [ 5631-96-9 ]
YieldReaction ConditionsOperation in experiment
98% With boron trichloride; In neat (no solvent); at 20℃; for 0.216667h;Green chemistry; General procedure: To a mixture of 1, 2, 3, benzylic, allylicalcohol or symmetric diol (1 mmol) and THP(1 mmol), bismuth trichloride (5 mol %) was added.Then the reaction mixture was stirred for appropriatetime as given in Table 1 at room temperature. Thereaction as monitored by TLC. After completion ofthe reaction it was poured into water and the productwas extracted with ethyl acetate (3x25 mL). Laterthe organic layer was washed with brine, dried withanhydrous sodium sulphate and concentrated invacuum to obtain the crude mass. Which was furtherpurifed by silica gel column chromatography(1:9EtOAc, hexane)to afford the corresponding THPether. Finally the products were characterized using1H NMR and Mass spectra.
94.6% With toluene-4-sulfonic acid; at 0 - 20℃; for 2h; 2-Chloroethanol (100 mL, 1.49 mol), 3,4-dihydro-2H-pyran (150 mL, 1.65 mol), and p-TsOH.H2O (250 mg) were mixed at 0 C and allowed to warm up to room temperature. After 2 h, the mixture was dissolved in Et2O (100 mL), washed with saturated aqueous NaHCO3 (3 x 100 mL), and vacuum distilled (92 C) to yield 2-(2-chloroethoxy)tetrahydropyran (1) (232 g, 94.6 %) as a colorless liquid: 1H NMR (500 MHz, CDCl3) delta 1.49 - 1.85 (m, 6H), 3.48 - 3.96 (m, 6H), 4.64 (t, J = 3.7 Hz, 1H); 13C NMR (125 MHz, CDCl3) delta 99.1, 67.7, 62.3, 43.3, 30.5, 25.5, 19.4.
88% With Amberlyst H-15; In dichloromethane; at 25℃; for 17.25h; 2-Chloro-1-ethanol (21.74 g, 0.27 mol), dichloromethane (50 mL) and Amberlyst H-15 (1 g) were added to the reaction flask. Then, 3,4-dihydro-2H-pyran (25 mL, 0.27 mol) was added over 15 minutes. The reaction mixture was stirred at 25 C for 17 hours. After filtering Amberlyst H-15, dichloromethane was evaporated in vacuo to obtain 2-(2-chloroethoxy)tetrahydro-2H-pyran (Compound 3), 39.12 g. The yield was 88%. Used directly in the next step without purification.
With amberlyst H-15; In dichloromethane; at 25℃; for 17h; 2-Chloro-1-ethanol (21.74 g, 0.27 mol),Dichloromethane (50 mL) and Amberlyst H-15 (1 g) were added to the reaction flask, then 3,4-dihydro-2H-pyran (25 mL, 0.27 mol) was added over 15 min.The reaction mixture was stirred at 25 C for 17 hours.After filtering off Amberlyst H-15, the dichloromethane was evaporated in vacuo.2-(2-chloroethoxy)tetrahydro-2H-pyran (compound 3) is obtained,39.12g. The yield was 88%. It was used directly in the next step without purification.

Reference： [1]Oriental Journal of Chemistry,2017,vol. 33,p. 1030 - 1034
[2]Synthetic Communications,1995,vol. 25,p. 2211 - 2215
[3]Tetrahedron,1995,vol. 51,p. 4161 - 4172
[4]Tetrahedron Letters,2012,vol. 53,p. 5475 - 5478
[5]Canadian Journal of Chemistry,2008,vol. 86,p. 1099 - 1104
[6]Patent: CN108774215,2018,A .Location in patent: Paragraph 0021-0024
[7]Organic Preparations and Procedures International,1996,vol. 28,p. 613 - 617
[8]Phosphorus, Sulfur and Silicon and the Related Elements,2004,vol. 179,p. 2149 - 2152
[9]Liebigs Annalen der Chemie,1983,p. 770 - 801
[10]Synlett,1999,p. 1261 - 1262
[11]Tetrahedron Letters,1998,vol. 39,p. 9287 - 9288
[12]Macromolecules,2004,vol. 37,p. 5133 - 5135
[13]Patent: CN108912116,2018,A .Location in patent: Paragraph 0022; 0023; 0024
  • 8
  • [ 638-56-2 ]
  • [ 5631-96-9 ]
  • [ 2615-15-8 ]
Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 2186 - 2196
  • 9
  • [ 5631-96-9 ]
  • [ 112-60-7 ]
  • [ 42607-88-5 ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
  • 10
  • [ 5631-96-9 ]
  • [ 112-60-7 ]
  • [ 2615-15-8 ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
  • 11
  • [ 5631-96-9 ]
  • [ 121756-52-3 ]
  • [ 121756-54-5 ]
Reference： [1]Chemische Berichte,1989,vol. 122,p. 2147 - 2158
  • 12
  • [ 5631-96-9 ]
  • [ 16000-71-8 ]
  • 9-[2-(Tetrahydro-pyran-2-yloxy)-ethoxy]-hexadecan-8-ol [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
  • 13
  • [ 5631-96-9 ]
  • [ 20653-90-1 ]
  • [ 118832-44-3 ]
  • [ 118832-43-2 ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
  • 14
  • [ 5631-96-9 ]
  • [ 20653-90-1 ]
  • [ 118832-44-3 ]
  • [ 118832-43-2 ]
  • [ 118832-40-9 ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
[2]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
  • 15
  • [ 5631-96-9 ]
  • [ 20653-90-1 ]
  • 3-[2-(Tetrahydro-pyran-2-yloxy)-ethoxy]-octan-2-ol [ No CAS ]
  • 2-[2-(Tetrahydro-pyran-2-yloxy)-ethoxy]-octan-3-ol [ No CAS ]
  • C22H42O6 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
[2]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
[3]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
  • 16
  • [ 5631-96-9 ]
  • [ 13071-59-5 ]
  • C24H38O7 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
  • 17
  • [ 5631-96-9 ]
  • [ 92-69-3 ]
  • [ 126301-69-7 ]
Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1989,vol. 44,p. 983 - 987
  • 18
  • [ 5631-96-9 ]
  • [ 2612-30-8 ]
  • C24H38O6 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
  • 19
  • [ 5631-96-9 ]
  • [ 4270-73-9 ]
  • [ 137378-15-5 ]
Reference： [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1387 - 1394
  • 20
  • [ 5631-96-9 ]
  • [ 831-82-3 ]
  • [ 126301-65-3 ]
Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1989,vol. 44,p. 983 - 987
  • 21
  • [ 5631-96-9 ]
  • [ 17401-06-8 ]
  • [ 83892-76-6 ]
Reference： [1]Synthesis,1982,p. 782 - 785
  • 22
  • [ 5631-96-9 ]
  • [ 79299-29-9 ]
  • [ 122800-59-3 ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 4914 - 4929
  • 23
  • [ 5631-96-9 ]
  • [ 1460-57-7 ]
  • C20H36O6 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
  • 24
  • [ 5631-96-9 ]
  • [ 134167-10-5 ]
  • 2-[2-((S)-2-Azido-3-benzyloxy-propoxy)-ethoxy]-tetrahydro-pyran [ No CAS ]
Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 1283 - 1286
  • 25
  • [ 5631-96-9 ]
  • [ 55063-81-5 ]
  • [ 82265-05-2 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 3478 - 3486
  • 26
  • [ 5631-96-9 ]
  • [ 87033-40-7 ]
  • [ 87033-58-7 ]
Reference： [1]Collection of Czechoslovak Chemical Communications,1983,vol. 48,p. 1187 - 1211
  • 27
  • [ 5631-96-9 ]
  • [ 87033-40-7 ]
  • [ 345939-13-1 ]
Reference： [1]Collection of Czechoslovak Chemical Communications,1983,vol. 48,p. 1187 - 1211
  • 28
  • [ 5631-96-9 ]
  • [ 80525-60-6 ]
  • [ 94650-69-8 ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
[2]Synthesis,1984,vol. NO. 9,p. 776 - 778
  • 29
  • [ 5631-96-9 ]
  • [ 103772-77-6 ]
  • [ 110027-14-0 ]
Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 1995 - 1998
  • 30
  • [ 5631-96-9 ]
  • [ 96574-08-2 ]
  • [ 77544-65-1 ]
Reference： [1]Chemische Berichte,1985,vol. 118,p. 914 - 921
  • 31
  • [ 5631-96-9 ]
  • [ 96574-04-8 ]
  • [ 96574-05-9 ]
Reference： [1]Chemische Berichte,1985,vol. 118,p. 914 - 921
  • 32
  • [ 5631-96-9 ]
  • [ 93622-61-8 ]
  • [ 93622-44-7 ]
Reference： [1]Bulletin of the Chemical Society of Japan,1984,vol. 57,p. 1976 - 1984
  • 33
  • [ 5631-96-9 ]
  • [ 6581-66-4 ]
  • [ 107-07-3 ]
Reference： [1]Acta Chimica Hungarica,1983,vol. 112,p. 233 - 240
  • 34
  • [ 5631-96-9 ]
  • [ 120-80-9 ]
  • [ 116893-51-7 ]
Reference： [1]Gazzetta Chimica Italiana,1987,vol. 117,p. 717 - 722
  • 35
  • [ 5631-96-9 ]
  • [ 10041-02-8 ]
  • [ 1026410-14-9 ]
Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4790 - 4794
  • 36
  • [ 5631-96-9 ]
  • [ 504-63-2 ]
  • C17H32O6 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
  • 37
  • [ 5631-96-9 ]
  • [ 513-85-9 ]
  • C18H34O6 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 857 - 860
  • 38
  • [ 5631-96-9 ]
  • [ 602-09-5 ]
  • C34H38O6 [ No CAS ]
Reference： [1]Bulletin of the Chemical Society of Japan,1983,vol. 56,p. 3672 - 3678
  • 39
  • [ 5631-96-9 ]
  • [ 105-53-3 ]
  • [ 25823-84-1 ]
Reference： [1]Tetrahedron,1995,vol. 51,p. 4161 - 4172
  • 40
  • [ 5631-96-9 ]
  • [ 13411-42-2 ]
  • [ 174710-22-6 ]
Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 1794 - 1805
  • 41
  • [ 5631-96-9 ]
  • [ 533-58-4 ]
  • [ 196106-21-5 ]
Reference： [1]Tetrahedron,1997,vol. 53,p. 11881 - 11898
  • 42
  • [ 5631-96-9 ]
  • [ 38941-98-9 ]
  • [ 196106-20-4 ]
Reference： [1]Tetrahedron,1997,vol. 53,p. 11881 - 11898
  • 43
  • [ 5631-96-9 ]
  • [ 103-16-2 ]
  • [ 205381-75-5 ]
Reference： [1]Canadian Journal of Chemistry,1998,vol. 76,p. 1429 - 1436
  • 44
  • [ 5631-96-9 ]
  • [ 2150-44-9 ]
  • 3,5-bis-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-benzoic acid methyl ester [ No CAS ]
Reference： [1]Canadian Journal of Chemistry,1998,vol. 76,p. 1429 - 1436
  • 45
  • [ 5631-96-9 ]
  • [ 123-31-9 ]
  • C20H30O6 [ No CAS ]
Reference： [1]Canadian Journal of Chemistry,1998,vol. 76,p. 1429 - 1436
  • 46
  • [ 5631-96-9 ]
  • [ 86259-87-2 ]
  • 2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-tetrahydro-pyran [ No CAS ]
  • [ 230620-74-3 ]
Reference： [1]Synthetic Communications,1999,vol. 29,p. 2337 - 2347
  • 47
  • [ 5631-96-9 ]
  • [ 86259-87-2 ]
  • [ 230620-74-3 ]
Reference： [1]Synthetic Communications,1999,vol. 29,p. 2337 - 2347
YieldReaction ConditionsOperation in experiment
11 g (67%) 1-Chloro-2-(tetrahydropyranyl)oxy-ethane (29) 1-Chloro ethanol (8.06 g, 100 mmol) was dissolved in dry CH2 Cl2 (100 ml) and cooled to 0 C. in an ice bath under argon. To this stirred solution was added dihydropyran (12.6 g, 150 mmol) followed by pyridinium -p-toluene -4-sulfonate (1.25 g, 5 mmol) and the stirring continued for overnight. The reaction mixture was evaporated to dryness and dissolved in EtOAc (200 ml). The EtOAC extract was washed with 5% NaHCO3 solution (100 ml), water (100 ml) and brine (100 ml). The organic extract was dried and evaporated to dryness. The crude material was purified by flash chromatography over silica gel using hexane?CH2 Cl2 as the eluent. The pure fractions collected together and evaporated to give 11 g (67%) of pure product.
  • 50
  • [ 5631-96-9 ]
  • [ 67583-61-3 ]
  • [ 244296-94-4 ]
Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 276 - 286
[2]Organic Letters,1999,vol. 1,p. 791 - 794
[3]Chemical Communications,2000,p. 863 - 864
  • 51
  • [ 5631-96-9 ]
  • [ 137915-54-9 ]
  • [ 357670-24-7 ]
Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 5113 - 5123
[2]Chemical Communications,2000,p. 863 - 864
  • 52
  • [ 5631-96-9 ]
  • [ 104286-24-0 ]
  • [ 244296-95-5 ]
Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 276 - 286
[2]Organic Letters,1999,vol. 1,p. 791 - 794
[3]Chemical Communications,2000,p. 863 - 864
  • 53
  • [ 5631-96-9 ]
  • sym-(hydroxy)di[4-tert-butylbenzo]-16-crown-5 [ No CAS ]
  • 2-[sym-di[4-tert-butylbenzo]-16-crown-5-oxy]-ethanol tetrahydropyranyl ether [ No CAS ]
Reference： [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 1337 - 1350
  • 54
  • [ 5631-96-9 ]
  • [ 141-78-6 ]
  • [ 542-58-5 ]
Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 355 - 357
  • 55
  • [ 5631-96-9 ]
  • [ 41502-60-7 ]
  • [ 357670-31-6 ]
Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 5113 - 5123
  • 56
  • [ 5631-96-9 ]
  • [ 121676-26-4 ]
  • [ 357670-34-9 ]
Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 5113 - 5123
  • 57
  • [ 5631-96-9 ]
  • [ 357670-30-5 ]
  • [ 357670-33-8 ]
Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 5113 - 5123
  • 58
  • [ 5631-96-9 ]
  • [ 357670-29-2 ]
  • [ 357670-32-7 ]
Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 5113 - 5123
  • 59
  • [ 5631-96-9 ]
  • [ 1707-77-3 ]
  • 3,4-bis-O-(2-O-tetrahydropyranyloxyethyl)-1,2:5,6-di-O-isopropylidene-D-mannitol [ No CAS ]
Reference： [1]Tetrahedron Asymmetry,2001,vol. 12,p. 1763 - 1769
  • 60
  • [ 864719-80-2 ]
  • [ 5631-96-9 ]
  • [ 864719-81-3 ]
Reference： [1]Tetrahedron,2005,vol. 61,p. 8177 - 8191
  • 61
  • [ 5631-96-9 ]
  • [ 107-07-3 ]
YieldReaction ConditionsOperation in experiment
98% With methanol; boron trichloride; In neat (no solvent); at 20℃; for 0.05h;Green chemistry; General procedure: To the above THP ether solution(1 mmol)in methanol (10 mL),5 mol % bismuth trichloridewas added. The reaction mixture was stirred forappropriate time as provided in Table 1 at roomtemperature. The reaction was monitored by TLC.After completion of the reaction water was added tothe reaction mixture and the product was extractedwith ethyl acetate (3x25 mL). Later the combinedorganic layer was washed with brine, dried overanhydrous sodium sulphate and concentrated invacuum to give a crude mass, which was purifedover silica gel column to afford parent alcohol inquantitative yield.
Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2006,vol. 45,p. 305 - 308
[2]Oriental Journal of Chemistry,2017,vol. 33,p. 1030 - 1034
  • 62
  • [ 5631-96-9 ]
  • [ 112-35-6 ]
  • [ 727986-31-4 ]
Reference： [1]Macromolecules,2004,vol. 37,p. 5133 - 5135
  • 63
  • [ 5631-96-9 ]
  • [ 111-45-5 ]
  • [ 727986-30-3 ]
Reference： [1]Macromolecules,2004,vol. 37,p. 5133 - 5135
  • 64
  • [ 5631-96-9 ]
  • [ 201995-24-6 ]
  • 2-[2-(2-undecyloxy-1-undecyloxymethyl-ethoxy)-ethoxy]-tetrahydro-pyran [ No CAS ]
Reference： [1]Carbohydrate Research,2006,vol. 341,p. 823 - 835
  • 65
  • [ 5631-96-9 ]
  • [ 196106-33-9 ]
Reference： [1]Tetrahedron,1997,vol. 53,p. 11881 - 11898
  • 66
  • [ 329216-67-3 ]
  • [ 5631-96-9 ]
  • [ 848888-35-7 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In water; at 60℃; for 6h;Product distribution / selectivity; EXAMPLE 1 LL- (4- [2- (2-HYDROXYETHOXY) ETHYL]-L- piperazinyl) dibenzo (b, f] [1, 4] thiazepine (base Quetiapine) To 26.2 mL of 50% aqueous solution of sodium hydroxide are added successively 5 G (14.7 mmols) de 2- (4- dibenzo [b, f] [1, 4] THIAZEPINE-11-IL-PIPERAZINE-L-IL) ethanol, 10.43 g (63.4 mmols) of 2- (2-CHLOROETHOXY)-TETRAHYDRO-2H- pyrane and 0. 49 g of tetrabutyl ammonium hydrogen sulphate. The mixture is heated at 60C for 6 hours with thorough stirring. It is cooled to 20-25C, and 45 mL de toluene and 26 mL of water are added while agitating. The phases are separated and the organic phase is washed with water (2 x 26 ML). 32 mL of water and 5 mL of 35% hydrochloric acid 35% are added and the two-phase mixture is stirred at 20-25C for 3 hours. The phases are separated and the aqueous phase is washed successively with n-butanol (10 mL) and toluene (10 ML). Then 45 ML OF toluene and 10% aqueous solution of potassium carbonate are added until the aqueous phase pH 10 is reached. The phases are separated and the aqueous phase is extracted with toluene (10 mL). The combined organic phases are evaporated to dryness under vacuum, yielding 4.80 g (85%) of the product of the title as a light yellow oil.
With potassium hydroxide;Aliquat 336; at 40℃; for 20h;Product distribution / selectivity; EXAMPLE 3 ll- (4- [2- (2-hydroxyethoxy) ethyl]-l- piperazinyl) dibenzo [b, f] [1, 43thiazepine (base Quetiapine) To 10.43 g (63.4 MMOLS) OF 2- (2-CHLOROETHOXY)-TETRAHYDRO- 2H-pyrane are added successively 5 g (14. 7 mmols) of 2- (4- dibenzo [b, f] [1.4] THIAZEPINE-11-IL-PIPERAZINE-1-IL) ethanol, 5 g of powdered potassium hydroxide and 0.49 g of Aliquat 336 catalyst. The mixture is heated at 40C for 20 hours with thorough stirring. The synthesis proceeds as in Example 1, yielding 4.23 g (75%) of the product of the title as a light yellow oil, having IR AND 1H-RMN spectra identical to those of the product obtained in Example 1.
With potassium hydroxide;18-crown-6 ether; at 40℃; for 6h;Product distribution / selectivity; EXAMPLE 2 ll- (4- [2- (2-hydroxyethoxy) ethyl]-l- piperazinyl) dibenzo [b, f] [1, 4] thiazepine (base Quetiapine) To 10.43 g (63.4 mmols) of 2- (2-CHLOROETHOXY)-TETRAHYDRO- 2H-pyrane are added successively 5 g (14. 7 mmols) of 2- (4- dibenzo [B, F] [1. 4] THIAZEPINE-11-IL-PIPERAZINE-1-IL) ethanol, 5 g of powdered potassium hydroxide and 0.49 g 18-corona-6 catalyst. The mixture is heated at 40C for 6 hours with thorough stirring. The synthesis proceeds as in Example 1, yielding 4.65 g (82%) of the product of the title as a light yellow oil, having IR AND 1H-RMN SPECTRA identical to those of the product obtained in Example 1.
Reference： [1]Patent: WO2005/14590,2005,A2 .Location in patent: Page/Page column 10
[2]Patent: WO2005/14590,2005,A2 .Location in patent: Page/Page column 11
[3]Patent: WO2005/14590,2005,A2 .Location in patent: Page/Page column 11
  • 67
  • [ 5631-96-9 ]
  • (+/-)-3-(trans-3,4-dimethylpiperidinyl)phenol [ No CAS ]
  • (+/-)-3-{1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-trans-3,4-dimethylpiperidinyl}phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium iodide; sodium hydrogencarbonate; In water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; Example 19 (+-)-3-{1-[2-(Tetrahydro-2H-pyran-2-yloxy)ethyl]-trans-3,4-dimethylpiperidinyl}phenol To a solution of (+-)-3-(trans-3,4-dimethylpiperidinyl)phenol (60 mg, 0.29 mmol) in N,N-dimethylformamide (2.5 mL) at room temperature was added sodium hydrogencarbonate (27 mg, 0.32 mmol), sodium iodide (48 mg, 0.32 mmol) and <strong>[5631-96-9]2-chloroethyl tetrahydro-2H-pyran-2-yl ether</strong> (52 mg, 0.32 mmol) in N,N-dimethylformamide (2.0 mL). The mixture was heated at 120 C. for 1.5 hours, cooled and then water (30 mL) and ethyl acetate (10 mL) were added. The two layers were separated and the aqueous layer was extracted with ethyl acetate (2*10 mL) and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude oil. This was purified by preparative HPLC on a Dynamax column, 42*250 mm; flow 8.0 mL min-1; employing U.V. detection at 275 nm; eluant gradient of acetonitrile:0.05 M aqueous ammonium acetate solution (90:10 to 10:90) to afford the title compound as its acetate salt. 1H-NMR (selected data from the acetate salt): 0.81 (d, 3H), 1.30 (s, 3H), 1.40-1.92 (m, 7H), 2.01-2.10 (m, 1H), 2.35 (m, 1H), 2.50-2.82 (m, 5H), 2.98 (m, 1H), 3.42-3.62 (m, 2H), 3.82-3.95 (m, 2H), 4.60 (m, 1H), 6.64 (d, 1H), 6.70-6.83 (m, 2H), 7.15 (t, 1H). MS (APCI+): m/z [MH+] 334.4; C20H31NO3+H requires 334.2.
Reference： [1]Patent: US6518282,2003,B1
  • 68
  • [ 5631-96-9 ]
  • [ 79722-21-7 ]
  • [ 179472-19-6 ]
YieldReaction ConditionsOperation in experiment
6.0 g (66%) With NaH; In water; ethyl acetate; N,N-dimethyl-formamide; N-tert-Butyloxycarbonyl-N-[(tetrahydropyranyl)oxy] ethyl-O-benzylhydroxylamine (30) To a stirred solution of N-tert-butyloxycarbonyl-O-benzylhydroxylamine 28 (5.79 g, 25.96 mmol) in dry DMF (50 ml) was added NaH (60%, 1.2 g, 30 mmol) slowly during 15 min period under argon atmosphere at 0 C. The reaction was allowed to stir at 0 C. for 30 min and at room temperature for 1 h. 1-Chloro-2-(tetrahydropyranyl)oxy-ethane 29 (4.95 g, 30 mmol) was added and the reaction mixture was heated at 80 C. for 12 h. The reaction was cooled and evaporated to dryness. The residue was suspended in water (50 ml), pH of the solution adjusted to 7 and extracted in EtOAc (150 ml). The EtOAc extract was washed with water and brine, dried and evaporated to dryness. The residue was purified by flash chromatography over silica gel using hexane?CH2 Cl2 as the eluent. The required fractions were collected and evaporated to give 6.0 g (66%) of an oily product. 1 H-NMR (CDCl3): delta1.48 (s, 9H, Boc), 1.49-1.84 (m, 6H, 3.CH2), 3.48-3.70 (m, 4H, 2.CH2), 3.86 (m, 2H, CH2), 4.60 (t, 1H, CH), 4.84 (s, 2H, CH2 Ph) and 7.32-7.42 (m, 5H, Ph).
Reference： [1]Patent: US5969135,1999,A
  • 69
  • [ 5631-96-9 ]
  • [ 112-30-1 ]
  • [ 23238-40-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; potassium hydroxide; tetrabutyl-ammonium chloride; In ethanol; toluene; a 3-Oxa-tridecan-1-ol 44.88 g (800 mmol) of fine powdered potassium hydroxide is added to 32.93 g (200 mmol) of the tetrahydropyranyl ether of 2-chloroethanol, 1 g (3.6 mmol) of tetrabutylammonium chloride and 20 g (126.36 mmol) of decan-1-ol in 300 ml of toluene, and it is refluxed for 24 hours. Solid is filtered out, and the filtrate is evaporated to the dry state. 500 ml of ethanol/50 ml of 10% aqueous hydrochloric acid are added to the residue (oil) that is thus obtained, and it is stirred for one hour at room temperature. It is evaporated to the dry state in a vacuum, and the residue is chromatographed on silica gel (mobile solvent: hexane/acetone=20:1). Yield; 21.73 g (85% of theory) of a colorless oil Elementary analysis: Cld: C 71.23 H 12.95; Fnd: C 71.05 H 13.10;
Reference： [1]Patent: US6083479,2000,A
  • 70
  • [ 5631-96-9 ]
  • [ 159660-88-5 ]
  • 6-(2-hydroxyethyl)-3-methyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione [ No CAS ]
  • 3-methyl-6-[2-(tetrahydropyran-2-yloxy)ethyl]-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N-methyl-acetamide; a 3-Methyl-6-[2-(tetrahydropyran-2-yloxy)ethyl]-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione 40 g of ethyldiisopropylamine and 52.5 g of 2-(2-chloroethoxy)tetrahydropyran (96% pure according to GC) were added to 54.5 g of 3-methyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione in 1.5 l of dimethylformamide, with stirring, and the mixture was heated for 30 h at 70 C. It was concentrated under vacuum, the residue was worked up by extraction with dichloromethane and water and the combined dichloromethane phases were dried and concentrated to give 25 g of 3-methyl-6-[2-(tetrahydropyran-2-yloxy) ethyl]-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione, which was purified by bulb-tube distillation at a bath temperature of 80 C. and 0.1 mbar and by column chromatography on aluminum oxide (activity grade III) and elution with dichloromethane/ethanol (volume ratio 95:5). 6-(2-Hydroxyethyl)-3-methyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione
Reference： [1]Patent: US5556854,1996,A
  • 71
  • [ 5631-96-9 ]
  • [ 132687-26-4 ]
  • [ 132686-80-7 ]
YieldReaction ConditionsOperation in experiment
In concentrated aqueous hydrochloric acid; ethanol; EXAMPLE 7 6,11-Dihydro-11-(2-hydroxyethyl)-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one Using a procedure analogous to that described in Example 2, 22.52 g (0.1 mol) of 6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one were convened to 6,11-dihydro-6-methyl-11-[2-[(2-tetrahydropyranyl)oxy]ethyl]-5H-pyrido-[2,3-b][1,5]benzodiazepin-5-one by reaction with 21.8 g (0.132 mol) of 1-chloro-2-[(2-tetrahydropyranyl)-oxy]-ethane. The raw material thus obtained was dissolved in a mixture of 500 ml ethanol and 100 ml of concentrated aqueous hydrochloric acid. After having been refluxed for two hours, the reaction mixture was evaporated in vacuo. The residue was triturated with ethanol, the precipitated crystals were faltered off and the solvent was removed from the filtrate by distillation in vacuo. The residue was purified by column chromatography on silica gel (0.2-0.5 mm) using chloroform/ethylacetate/methanol 5/5/1 (v/v/v) as an eluent. Colorless crystals of m.p. 133-134 C. (after recrystallization from xylene) were obtained in a yield of 9.0 g (33% of theory).
Reference： [1]Patent: US5571809,1996,A
  • 72
  • [ 5631-96-9 ]
  • [ 56341-41-4 ]
  • [ 20485-44-3 ]
  • [ 74-88-4 ]
  • 3,3-dimethyl-5-fluoro-1-(2-hydroxyethyl)-1,3-dihydro-2H-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium iodide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water; ethyl acetate; EXAMPLE 12 3,3-Dimethyl-5-fluoro-1-(2-hydroxyethyl)-1,3-dihydro-2H-indol-2-one: 5-Fluoro-1,3-dihydro-2H-indol-2-one (2.4 g, 15.9 mmol) (prepared according to the method of Clark et al., Synthesis (1991) 871) was dissolved in freshly distilled tetrahydrofuran with tetramethylethylenediamine (3.7 g, 31.9 mmol) and was cooled to -75 C. under nitrogen. nButyllithium (2.4 equivalents) was added and the mixture was stirred at -75 C. for 40 minutes. Iodomethane (9 g, 63 mmol) was added and the mixture was allowed to warm to room temperature. After two hours' stirring at this temperature, water (5 ml) was added and the mixture was concentrated under reduced pressure, the resulting oil was taken up in dichloromethane, washed with dilute hydrochloric acid, dried (MgSO4), filtered and concentrated to dry under reduced pressure to give a yellow oil. This oil was dissolved in N-methylpyrrolidone and stirred at room temperature under nitrogen. Sodium hydride (0.625 g, 15.6 mmol) was added and the mixture was stirred until gas evolution ceased. 2-(2-Chloroethoxy)tetrahydro-2H-pyran (2.5 g, 15 mmol) and sodium iodide (0.1 g, 0.66 mmol) was added and the mixture was warmed to 75 C. for 15 hours. Water was added and the mixture was concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed (*3) with water, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting oil was taken up in methanol, para toluenesulphonic acid (0.1 g, 0.5 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was concentrated under reduced pressure, taken up in ethyl acetate, washed (*3) with aqueous sodium hydrogen carbonate solution dried (MgSO4), filtered and concentrated under reduced pressure. The resulting oil was purified by column chromatography on silica gel, (eluent hexane/ethyl acetate) to give 3,3-dimethyl-5-fluoro-1-(2-hydroxyethyl)-1,3-dihydro-2H-indol-2-one as a yellow oil. MS shows 224 (MH+) base peak and 241 (M+NH4)
Reference： [1]Patent: US5773448,1998,A
  • 73
  • [ 5631-96-9 ]
  • [ 65347-55-9 ]
  • [ 345309-67-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In 4-methyl-2-pentanone; STEP A: 3-[1-(2-{2-tetrahydropyranyloxy}-ethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole A solution of 6.93 g of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole [described in French Pat. No. 2,362,628] dissolved at 100 C. in 70 ml of isobutyl methyl ketone admixed with 11.13 g of sodium carbonate and 14 ml of 2-(2-chloroethoxy)-tetrahydro-2H-pyran was refluxed with stirring under an inert atmosphere for 51/2 hours and was then cooled and poured into ice water. The mixture was extracted with ethyl acetate and the organic phase was washed with water, with aqueous sodium chloride solution, dried and evaporated to dryness. The 9.9 g of crystalline residue was chromatographed over silica gel and eluted with an 85-10-5 chloroform-acetonetriethylamine mixture to obtain 7.85 g of 3-[1-(2-{2-tetrahydropyranyloxy}-ethyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole in the form of crystals melting at 135 C.
Reference： [1]Patent: US4324790,1982,A
  • 74
  • [ 5631-96-9 ]
  • [ 3251-55-6 ]
  • 1-(4-acetamido-2-methoxyphenoxy)-2-(tetrahydropyran-2-yl-oxy)ethane [ No CAS ]
YieldReaction ConditionsOperation in experiment
82.5% With sodium hydroxide; In dimethyl sulfoxide; (1) 13.4 g of 4-acetamido-2-methoxyphenol are dissolved in 80 ml of dimethylsulfoxide under nitrogen atmosphere, and 2.96 g of powdery sodium hydroxide are added thereto. The mixture is stirred at 50 C. to 55 C. for 3 hours. A solution of 10 g of 2-chloro-1-(tetrahydropyran-2-yl-oxy)ethane in 20 ml of dimethylsulfoxide is added dropwise to the mixture, and said mixture is stirred at 100 C. for one hour. After the reaction, the mixture is poured into ice-water, and the aqueous mixture is extracted with ethyl acetate. The extract is washed with water and an aqueous saturated sodium chloride solution, successively. Said extract is dried and then evaporated under reduced pressure to remove the solvent. The residue is recrystallized from a mixture of ethyl acetate and n-hexane, whereby 15.5 g of 1-(4-acetamido-2-methoxyphenoxy)-2-(tetrahydropyran-2-yl-oxy)ethane are obtained as colorless needles. Yield: 82.5% M.p. 88 C.-90 C.
Reference： [1]Patent: US4413006,1983,A
  • 75
  • [ 5631-96-9 ]
  • 1,2,3,3a,4,5,6,7-octahydro-7-oxo-azepino[1,2,3-lm]-β-carboline [ No CAS ]
  • [ 75622-65-0 ]
YieldReaction ConditionsOperation in experiment
47% With potassium iodide; potassium carbonate; In N-methyl-acetamide; chloroform methanol; (1) 15 ml of dimethylformamide, 1.06 g of 2-(tetrahydropyran-2-yl-oxy)ethyl chloride, 0.97 g of potassium carbonate and 0.1 g of potassium iodide were added to 1.30 g of 1,2,3,3a,4,5,6,7-octahydro-7-oxo-azepino[1,2,3-lm]-beta-carboline, and the mixture was stirred at 80 C. for 4 hours. After the reaction was completed, the reaction mixture was poured into ice-water and the aqueous mixture was extracted with ethyl acetat. The extract was washed with water, dried and condensed. The oily residue thus obtained was purified by silica gel chromatography (Solvent: 1% methanol-chloroform), whereby 934 mg of 1,2,3,3a,4,5,6,7-octahydro-3-[2-(tetrahydropyran-2-yl-oxy)ethyl]-7-oxo-azepino[1,2,3-lm]-beta-carboline were obtained as an oil. Yield: 47% IRnumaxfilm (cm-1): 1695, 1620, 760 Mass (m/e): 368 (M+) NMR (delta, CDCl3): 8.67-8.30 (m, 1H, aromatic); 7.73-7.13 (m, 3H, aromatic); 4.63 (broad, 1H STR34 4.83-2.52 (m, 13H); 2.50-1.00 (m, 10H)
Reference： [1]Patent: US4228168,1980,A
  • 76
  • [ 5631-96-9 ]
  • [ 98704-58-6 ]
  • [ 1061302-90-6 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 8830 - 8840
  • 77
  • [ 5631-96-9 ]
  • [ 22408-41-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In water; benzene; at 60℃; for 6h; 2-(2-Chloroethoxy)tetrahydro-2H-pyran (148 g, 0.9 mol) was added to a mixture of aqueous sodium hydroxide solution (50 %, 888 ml), tetra-n-butylammonium hydrogen sulfate (305 g, 0.90 mol) and benzene (1480 ml) and the mixture was stirred at 600 C. After approx. 6 h, there was no more conversion (there was always starting material left). Diethyl ether (2 I) and water (2 I) were added and the phases were separated. The organic layer was washed with water (1 I) and the combined aqueous phases were extracted once with diethyl ether (1 I). The combined ethereal layers were dried over magnesium sulfate, and distilled with a vigreux column, first at normal pressure (most of the solvent - diethyl ether and benzene - was distilled off), then under reduced pressure, affording three fractions containing 2-(vinyloxy)tetrahydro-2/-/-pyran: F1 : 16 g (60mbar, 65 0C, 65 % product (+ benzene, 1H NMR) F2: 56 g (60mbar, 95 0C, 90 % product (+ tributylamine, 1H NMR) F3: 19 g (60-40mbar, 95 0C, 80 % product (+ tributylamine, 1H NMR)
Reference： [1]Patent: WO2008/95912,2008,A2 .Location in patent: Page/Page column 81
  • 78
  • [ 5631-96-9 ]
  • [ 1198765-09-1 ]
  • [ 1198765-10-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 90℃; The residue from the previous reaction (180 mg, 0.53 mmol, 1 eq.) was dissolved in a 1:1 mixture of DMF and THF, and 0.2 ml 2-(2-Chloro-ethoxy)-tetrahydro-pyran (3.2 mmol, 6 eq) was added, followed by 80 mg sodium hydride (95% dry, 3.2 mmol, 6 eq) and the mixtured heated to 90 C. overnight. Cooled, quenched 2 ml water, concentrated to dryness and loaded directly on a silica gel column, eluting with 50% ethyl acetate in hexanes to give 140 mg 6-{1,1-Dimethyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-ethyl}-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1-one. MS (ESI) 468.0 (M+H)+.
Reference： [1]Patent: US2010/222325,2010,A1 .Location in patent: Page/Page column 116-117
  • 79
  • [ 5631-96-9 ]
  • [ 1283056-78-9 ]
  • C78H96N2O18S2 [ No CAS ]
Reference： [1]Comptes Rendus Chimie,2011,vol. 14,p. 286 - 300
  • 80
  • [ 5631-96-9 ]
  • [ 1283056-68-7 ]
  • C74H96N2O19S2 [ No CAS ]
Reference： [1]Comptes Rendus Chimie,2011,vol. 14,p. 286 - 300
  • 81
  • [ 5631-96-9 ]
  • [ 2516-33-8 ]
  • [ 1354967-77-3 ]
YieldReaction ConditionsOperation in experiment
21% NaH 60% suspension in mineral oil (6.659 g, equivalent to 3.995 g of NaH, 0.166 mol, 1 .2 eq) was weighed into a flame-dried flask and washed with hexanes (2 x 50 mL) under nitrogen atmosphere. Residual hexanes were allowed to evaporate under nitrogen flow before suspending the NaH in dry THF and cooling to 0 C. 1 (10.000 g, 0.139 mol) was dissolved in dry THF (20 mL) and dry DMF (30 mL) before adding dropwise over 30 minutes to the suspended NaH with stirring. The mixture was brought to rt before dropwise addition of 2-chloroethoxytetrahydro--?/-/- pyran (30.71 mL 0.208 mol 1 .5 eq) in dry THF (20 mL) over 30 minutes. The mixture was stirred at rt overnight before quenching with MeOH (20 mL). All solvents were removed before dissolving the residue in Et20 (200 mL) and washing with water (2 x 150 mL) and brine (150 mL). After removal of solvent, the resulting crude oil was purified by flash column chromatography (eluent DCM) to give 5.878 g colourless oil.
Reference： [1]Patent: WO2012/4549,2012,A1 .Location in patent: Page/Page column 19
  • 82
  • [ 5631-96-9 ]
  • [ 1363568-38-0 ]
  • [ 1363568-39-1 ]
Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2012,vol. 55,p. 88 - 95
  • 83
  • [ 5631-96-9 ]
  • [ 1400998-11-9 ]
Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 5475 - 5478
  • 84
  • [ 5631-96-9 ]
  • [ 4733-50-0 ]
  • [ 1400998-10-8 ]
YieldReaction ConditionsOperation in experiment
57% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 60℃; for 96h; 2,3-Dicyanohydroquinone (10.0 g, 0.062 mol), K2CO3 (19.0 g, 0.137 mol), chloride 1 (22.6 g , 0.137 mol), and KI (100 mg) in 200 mL DMF were stirred at 60 C for 48 h, when additional chloride 1 (11.3 g, 0.068 mol, 1.1 equiv) was added. After 48 h, the mixture was poured onto ice (500 g) and filtered to yield a beige solid, which was recrystallized from MeOH to yield dinitrile 2 (14.8 g, 57 %) as a white crystalline solid: IR (neat) numax 2940, 2231 cm-1; 1H NMR (500 MHz, CDCl3) delta 1.54 - 1.80 (m, 12H), 3.53 - 4.28 (m, 12H), 4.71 (br s, 2H), 7.28 (s, 2H); 13C NMR (125 MHz, CDCl3) delta 155.5, 119.1, 113.1, 105.7, 99.4, 70.0, 65.6, 62.5, 30.6, 25.4, 19.5; MALDI-MS calcd. for C22H28N2NaO6: [M + Na]+ 439.5, found: 439.6; ESI-MS calcd. for C44H56N4NaO12: [2M + Na]+ 855.4, found: 854.9. ESI-HRMS calcd. for C22H28N2NaO6: [M + Na]+ 439.184, found: 439.1844; calcd. for C44H56N4NaO12: [2M + Na]+ 855.3787, found: 855.3786.
Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 5475 - 5478
  • 85
  • [ 851219-16-4 ]
  • [ 5631-96-9 ]
  • C43H67N3O8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 90℃;Inert atmosphere; General procedure: A mixture of 3 (2.64 g, 4.02 mmol), commercially available 2-(2-chloroethoxy) tetrahydro-2H-pyran (4) (0.79 g, 4.82 mmol), K2CO3 (1.11 g, 8.04 mmol) and KI (0.13 g, 0.80 mmol) in N,N-dimethylformamide (DMF) (40 mL) under argon was stirred overnight at 90C. After cooling to room temperature, themixture was diluted with CHCl3 (200 mL) and H2O (200 mL). The aqueous phase was extracted with CHCl3 (100 mL, twice), and the combined organic phases were washed with brine (50 mL), dried over MgSO4 and evaporated to give crude 5. Purification of the crude sample by column chromatography over silica gel (hexane/EtOAc) gave pure 5 (1.22 g, 39% yield).
Reference： [1]Biological and Pharmaceutical Bulletin,2015,vol. 38,p. 30 - 38
  • 86
  • [ 5631-96-9 ]
  • C44H63N5O10S2 [ No CAS ]
  • C51H75N5O12S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 90℃;Inert atmosphere; General procedure: A mixture of 3 (2.64 g, 4.02 mmol), commercially available 2-(2-chloroethoxy) tetrahydro-2H-pyran (4) (0.79 g, 4.82 mmol), K2CO3 (1.11 g, 8.04 mmol) and KI (0.13 g, 0.80 mmol) in N,N-dimethylformamide (DMF) (40 mL) under argon was stirred overnight at 90C. After cooling to room temperature, themixture was diluted with CHCl3 (200 mL) and H2O (200 mL). The aqueous phase was extracted with CHCl3 (100 mL, twice), and the combined organic phases were washed with brine (50 mL), dried over MgSO4 and evaporated to give crude 5. Purification of the crude sample by column chromatography over silica gel (hexane/EtOAc) gave pure 5 (1.22 g, 39% yield).
Reference： [1]Biological and Pharmaceutical Bulletin,2015,vol. 38,p. 30 - 38
  • 87
  • [ 5631-96-9 ]
  • 6-[1-[1-(5-hydroxy-2-pyridyl)pyrazol-3-yl]ethyl]-3-(2-trimethylsilylethoxymethyl)-1,3-benzothiazol-2-one [ No CAS ]
  • 6-[1-[1-[5-(2-tetrahydropyran-2-yloxyethoxy)-2-pyridyl]pyrazol-3-yl]ethyl]-3-(2-trimethylsilylethoxymethyl)-1,3-benzothiazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With caesium carbonate; In acetonitrile; at 90℃; for 3h; Add cesium carbonate (725.82 g, 2.23 mol) and 2-(2-chloroethoxy)tetrahydro-2H- pyran (183.37 g, 167.01 mL, 1.50 equiv) to a solution of 6-[1-[1-(5-hydroxy-2- pyridyl)pyrazol-3 -yl]ethyl] -3 -(2-trimethylsilylethoxymethyl)- 1,3 -benzothiazol-2-one (400g, 742.56 mmol) in acetonitrile (2 L). Stir the mixture at 90 C for 3 h. Cool down the reaction and add cyclohexane (4 L) and water (4 L) and separate phases. Re-extract the aqueous layer with cyclohexane (2.5 L) and evaporate the combined organic layers to afford the desired compound as a brown oil (420 g, 8 1%). M+1597.
Reference： [1]Patent: WO2015/183673,2015,A1 .Location in patent: Page/Page column 97; 98

Tags: 5631-96-9 synthesis path| 5631-96-9 SDS| 5631-96-9 COA| 5631-96-9 purity| 5631-96-9 application| 5631-96-9 NMR| 5631-96-9 COA| 5631-96-9 structure

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