HCID 56623966, compound → HCID 21279134, compound

HRID 2291641Notes

Reaction equation

HRID 2291641 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][C@H:22]1[O:26][C:25](=[O:27])[C@H:24](S(C2C=CC=CC=2)=O)[C@H:23]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH:22]1[O:26][C:25](=[O:27])[CH:24]=[C:23]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 56623966HCID 56623966, compound

Product 1

HCID 21279134HCID 21279134, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (3R*,4S*,5R*)-5-[3-(t-butyldiphenylsilyloxy)propyl]-2-oxo-4-phenyl-3- phenylsulfinyltetrahydrofuran (650 mg) in toluene (6.5 ml) was refluxed for 30 minutes. The reaction mixture was chromatographed on silica gel (20 g) eluting with a mixture of benzene and acetone (100:1 to 25:1) to give 5-[3-(t-butyldiphenylsilyloxy)propyl]-4-phenyl-2(5H)furanone (313 mg) as an oil.

Workup

  1. customThe reaction mixture was chromatographed on silica gel (20 g)
  2. washeluting with a mixture of benzene and acetone (100:1 to 25:1)

Sources & evidence

ORD record
ord-9e8b9455717c4d02bbd2c55883527671
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

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