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

HRID 271374Notes

Reaction equation

HRID 271374 reaction equation
C(Cl)Cl.[C:4]([O:12][CH:13]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1)(=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)C(C)C)(C)C.FC(F)(F)S(O[Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])(=O)=O>C(OCC)(=O)C.CCCCCC.O>[CH2:4]([O:12][CH:13]1[CH2:18][CH2:17][C:16]([O:19][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])=[CH:15][CH2:14]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 6344Dichloromethane2×HCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 2426774-(Benzoyloxy)cyclohexanone

Product 1

HCID 68669646{[4-(Benzyloxy)cyclohex-1-en-1-yl]oxy}(tert-butyl)dimethylsilaneYield 86.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A methylene chloride (200 mL) solution of 4-oxocyclohexyl benzoate [Macromolecules 2000, 33, 4619] (17.2 g, 84.5 mmol) in N,N-diisopropylethylamine (29.4 mL, 169 mmol) was cooled in an ice bath under nitrogen. A methylene chloride (50 mL) solution of tert-butyldimethylsilyl trifluormethanesulfonate (20.3 mL, 88.7 mmol) was added dropwise over 0.5 h. After warming to room temperature the contents of the reaction flask were poured into water. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Flash column chromatography (hexane:ethyl acetate, 95:5) gave a pale oil (23.2 g, 86% yield).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11ceb7693dac4012ab5b02ec9bc40270
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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