m-Chloroperbenzoic acid → HCID 11429988, compound

HRID 2087020Notes

Reaction equation

HRID 2087020 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([Cl:25])[C:16]=1[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])C=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC1C=CC=C([C:33]([O:35]O)=[O:34])C=1>ClCCl.O>[CH:33]([O:35][C:11]1[CH:14]=[C:15]([Cl:25])[C:16]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])=[C:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3])[CH:10]=1)=[O:34]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11269599HCID 11269599, compound

Product 1

HCID 11429988HCID 11429988, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.73 g (4.30 mmol) of 13 in 15 mL of dichloromethane under argon was added 2.03 g (6.50 mmol) of 55% m-chloroperbenzoic acid (MCPBA). After refluxing for 10 h, the solution was diluted with 30 mL of water and extracted three times with diethyl ether (50 mL each). The combined extracts were washed twice with saturated aqueous NaHCO3 (30 mL each), 30 mL of water, and 30 mL of brine, dried (MgSO4), concentrated, and column chromatographed on silica gel using hexane as eluent to give 1.24 g (70% yield) of 3,4-bis-(t-butyldimethylsilyloxy)-5-chlorophenyl formate. 1H NMR (CDCl3) δ 8.22 (s, 1H, CHO), 6.79 (d,J=3.2 Hz, 1H), 6.58 (d,J=3.2 Hz, 1H), 1.03 (s, 9H, t-Bu), 0.96 (s, 9H, t-Bu), 0.22 (s, 6H, Me), 0.19 (s, 6H, Me); 13C NMR (CDCl3) δ 159.0 (s, C═O), 148.8 (s), 143.0 (s), 142.4 (s), 127.1 (s), 115.5 (d), 113.1 (d), 26.2 (q, 6C, t-Bu), 18.8 (s, 2C, t-Bu), −3.3 (q, 2C, Me), −3.6 (q, 2C, Me).

Workup

  1. temperatureAfter refluxing for 10 h
  2. extractionextracted three times with diethyl ether (50 mL each)
  3. washThe combined extracts were washed twice with saturated aqueous NaHCO3 (30 mL each), 30 mL of water, and 30 mL of brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customcolumn chromatographed on silica gel

Sources & evidence

ORD record
ord-1f921bd96bf04638a0b647dabde55327
Source dataset
uspto-grants-2004_04
Patent number
US06727277B1

Reaction notes

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