Water → {[4-(Benzyloxy)cyclohex-1-en-1-yl]oxy}(tert-butyl)dimethylsilane

HRID 1970982Notes

Reaction equation

HRID 1970982 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Si:25](OS(C(F)(F)F)(=O)=O)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].O>C(Cl)Cl>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([O:15][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[CH:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 109873694-(Benzyloxy)cyclohexanone

Product 1

HCID 68669646{[4-(Benzyloxy)cyclohex-1-en-1-yl]oxy}(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-(benzyloxy)cyclohexanone (10 g, 49 mmol) and Hunig's base (17.1 mL, 98 mmol) in DCM (50 mL) was added TBSOTf (11.8 mL, 51.4 mmol) in DCM (50 mL) dropwise at 0° C. The reaction mixture was allowed to warm to room temperature, and left to stir until the reaction was complete. The mixture was poured into water, and the organic layer was separated, dried, and concentrated. Purification by flash chromatography afforded the title compound. 1H NMR (600 MHz, CDCl3) δ 7.20-7.36 (m, 5H); 4.72 (br s, 1H); 4.55 (s, 2H); 3.60 (m, 1H); 1.72-2.38 (series of m, 6H); 0.90 (s, 9H); 0.10 (s, 6H).

Workup

  1. waitleft
  2. customthe organic layer was separated
  3. customdried
  4. concentrationconcentrated
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-96fc2d9eab53417196588f7400fcbad0
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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