Methanol → 6-[(4-Chlorophenyl)sulfonyl]-6-(2-hydroxy methylphenyl)-1-hexanol

HRID 748821Notes

Reaction equation

HRID 748821 reaction equation
[Si]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]([S:33]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)(=[O:35])=[O:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CO>O1CCCC1>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([S:33]([CH:26]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH2:19][OH:18])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])(=[O:35])=[O:34])=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 597507576-[2-(t-Butyldiphenylsilyloxy)methylphenyl]-6-[(4-chlorophenyl)sulfonyl]-1-hexanol

Product 1

HCID 597508536-[(4-Chlorophenyl)sulfonyl]-6-(2-hydroxy methylphenyl)-1-hexanolYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In tetrahydrofuran (5 ml) was dissolved 6-[2-(t-butyldiphenylsilyloxy)methylphenyl]-6-[(4-chlorophenyl)sulfonyl]-1-hexanol (200 mg, 0.322 mmol), followed by the dropwise addition of a tetrahydrofuran solution (1.0M, 0.7 ml, 0.7 mmol) of tetrabutylammonium fluoride under ice cooling. The resulting mixture was stirred at room temperature for 1 hour. Water (0.2 ml) was then added. 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=30:1 eluate was concentrated under reduced pressure, whereby the title compound (86 mg, 0.23 mmol, 70%) 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-316cccd9795c4a30931a7c0a536c1c68
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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