Triethylamine → 6-[2-(t-Butyldiphenylsilyloxy)methylphenyl]-6-[(4-chlorophenyl)sulfonyl]-1-hexanol

HRID 748820Notes

Reaction equation

HRID 748820 reaction equation
C([Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][O:32][Si:33]([C:46]([CH3:49])([CH3:48])[CH3:47])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[S:15]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])(C)C)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CO>[Si:33]([O:32][CH2:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH:14]([S:15]([C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)(=[O:16])=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:8])([C:46]([CH3:49])([CH3:47])[CH3:48])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 59750749t-Butyl [[6-[2-[(t-butyldiphenylsilyloxy) methyl]phenyl]-6-[(4-chlorophenyl)sulfonyl]hexyl]oxy]dimethylsilane

Product 1

HCID 597507576-[2-(t-Butyldiphenylsilyloxy)methylphenyl]-6-[(4-chlorophenyl)sulfonyl]-1-hexanolYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In methanol (30 ml) was dissolved t-butyl [[6-[2-[(t-butyldiphenylsilyloxy)methyl]phenyl]-6-[(4-chlorophenyl)sulfonyl]hexyl]oxy]dimethylsilane (830 mg, 1.13 mmol), followed by the addition of p-toluenesulfonic acid monohydrate (25 mg, 0.13 mmol). The resulting mixture was stirred at room temperature for 2 hours. Triethylamine (0.080 ml, 0.57 mmol) was added and then, the residue obtained by concentrating the resulting mixture under reduced pressure was subjected to flash silica gel chromatography. The fraction obtained from the dichloromethane:methanol=100:1 eluate was concentrated under reduced pressure, whereby the title compound (580 mg, 0.934 mmol, 83%) was obtained as a colorless oil.

Workup

  1. customthe residue obtained
  2. concentrationby concentrating the resulting mixture under reduced pressure
  3. customThe fraction obtained from the dichloromethane

Sources & evidence

ORD record
ord-8dc25c029b4a402f9f63df6aeacefba1
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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