Methanol → HCID 59750724, compound

HRID 748818Notes

Reaction equation

HRID 748818 reaction equation
C([Si]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]([S:35]([C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH2:27][CH2:28][CH2:29][CH2:30][S:31]([CH3:34])(=[O:33])=[O:32])(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CO>O1CCCC1>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([S:35]([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][S:31]([CH3:34])(=[O:33])=[O:32])(=[O:36])=[O:37])=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59750831HCID 59750831, compound

Product 1

HCID 59750724HCID 59750724, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In tetrahydrofuran (5 ml) was dissolved t-butyl [[2-[1-[(4-chlorophenyl)sulfonyl]-5-(methylsulfonyl)pentyl]benzyl]oxy]diphenylsilane (175 mg, 0.261 mmol). Under ice cooling, a tetrahydrofuran solution (1.0M, 0.6 ml, 0.6 mmol) of tetrabutylammonium fluoride was added dropwise to the resulting solution. The resulting mixture was then stirred at room temperature for 1 hour. After addition of water (0.5 ml), 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 (87 mg, 0.20 mmol, 61%) was obtained as a pale yellowish brown 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-68e22640f6eb4b798a73790dca4915d5
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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