Diethyl Ether → HCID 86742666, compound

HRID 2291625Notes

Reaction equation

HRID 2291625 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.[Si:12]([O:29][CH2:30][CH2:31][CH2:32][CH:33]=CC1C=CC=CC=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)C.S(=O)(O)[O-].[Na+]>ClCCl>[Si:12]([O:29][CH2:30][CH2:31][CH2:32][CH:33]1[O:10][CH:8]1[C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1)([C:25]([CH3:26])([CH3:27])[CH3:28])([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 54447315HCID 54447315, compound

Product 1

HCID 86742666HCID 86742666, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperbenzoic acid (2.14 g) was added to a solution of 5-(t-butyldiphenylsilyloxy)-1-phenyl-1-pentene (3.30 g) in dichloromethane (65 ml) at ambient temperature and the resulting mixture was stirred at the same temperature for 2 hours. The reaction mixture was poured into a mixture of diethyl ether and 5% aqueous sodium bisulfite (100 ml). The organic layer was separated, washed with aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, and evaporated in vacuo to give (2R*, 3R*)-3-[3-(t-butyldiphenylsilyloxy)propyl]-2-phenyloxirane (3.45 g) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with aqueous sodium bicarbonate, water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a11a92d922f740a28d4f5f4ea58a1e46
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

Loading…