m-Chloroperbenzoic acid → HCID 13486346, compound

HRID 2291640Notes

Reaction equation

HRID 2291640 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Si](OCCC[C@H:33]1[O:37][C:36](=[O:38])[C@H:35]([S:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:34]1[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.S(=O)(O)[O-].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)C>[O:38]=[C:36]1[CH:35]([S:39]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:9])[CH:34]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:33][O:37]1

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 57176698HCID 57176698, compound

Product 1

HCID 13486346HCID 13486346, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

m-Chloroperbenzoic acid (242 mg) was added to a solution of (3R*,4S*,5R*)-5-[3-(t-butyldiphenylsilyloxy)propyl] -2-oxo-4-phenyl-3-phenylthiotetrahydrofuran in dichloromethane (10 ml) at 0° C. and the resulting mixture was stirred at 0° C. for 30 minutes. The resulting mixture was poured into a mixture of diethyl ether, aqueous sodium bisulfite and aqueous sodium bicarbonate. The organic layer was separated, washed with water and brine successively, dried over ( magnesium sulfate, and evaporated in vacuo to give (3R*,4S*,5R*)-5-[3-(t-butyldiphenylsilyloxy)propyl]-2(oxo-4-phenyl-3-phenylsulfinyltetrahydrofuran (537 mg) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine successively
  3. dry with materialdried over ( magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-3b1272cbeb9440c087ad461197349ef6
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

Loading…