m-Chloroperbenzoic acid → 3-[Tert-butyl(diphenyl)silyl]oxycyclobutyl acetate

HRID 1692946Notes

Reaction equation

HRID 1692946 reaction equation
[Si:1]([O:18][CH:19]1[CH2:22][CH:21](C(=O)C)[CH2:20]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.C(=O)(O)[O-].[Na+].ClC1C=CC=[C:34]([C:38]([O:40]O)=[O:39])C=1>ClCCl>[C:38]([O:40][CH:21]1[CH2:20][CH:19]([O:18][Si:1]([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:22]1)(=[O:39])[CH3:34]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium Bicarbonate2×HCID 668242881-(3-[Tert-butyl(diphenyl)silyl]oxycyclobutyl)ethanone

Product 1

HCID 668244813-[Tert-butyl(diphenyl)silyl]oxycyclobutyl acetateYield 45.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(3-[tert-butyl(diphenyl)silyl]oxycyclobutyl)ethanone (0.65 g, 0.0018 mol) in dichloromethane (10 mL) at 0° C. was added sodium bicarbonate (0.39 g, 0.0046 mol) and m-chloroperbenzoic acid (1.0 g, 0.0046 mol) with stirring. The reaction was stirred at rt over night. LCMS showed incomplete reaction, another 2.5 eq. of mCPBA and NaHCO3 were added and the reaction was stirred for another day. The reaction was quenched with 20% aq. Na2S2O3 solution (50 mL) and stirred for a further 30 min at rt, then extracted with dichloromethane. The combined organic layers were washed with brine, dried over MgSO4, concentrated and purified on silica gel with Combiflash (silica gel, 0-10% EtOAc/Hex) to give the desired product (0.3 g, 40%) as colorless oil. LCMS calculated for C22H29O3Si(M+H)+: 369.2; Found: 369.4.

Workup

  1. stirringThe reaction was stirred at rt over night
  2. customreaction
  3. stirringthe reaction was stirred for another day
  4. customThe reaction was quenched with 20% aq. Na2S2O3 solution (50 mL)
  5. stirringstirred for a further 30 min at rt
  6. extractionextracted with dichloromethane
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. custompurified on silica gel with Combiflash (silica gel, 0-10% EtOAc/Hex)

Sources & evidence

ORD record
ord-fc630fde505347309e030ade663e6086
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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