4-tert-Butylcyclohexanone → HCID 10935034, compound

HRID 2355996Notes

Reaction equation

HRID 2355996 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C1(N[S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[F:23][C:22]([F:25])([F:24])[S:19]([O:11][C:8]1[CH2:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10][CH:9]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 73924-tert-ButylcyclohexanoneHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 10935034HCID 10935034, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A −78° C. solution of 4-tert-butylcyclohexanone (1.54 g, 10 mmol) and N-phenyl(trifluoromethanesulfonamide) (3.75 g, 10.5 mmol) in THF (20 mmol) was treated with 1M NaHMDS in THF (11 mL), warmed to room temperature, filtered through a pad of silica gel (10 g) with diethyl ether (5 mL), and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1% ethyl acetate/hexanes to provide the desired product.

Workup

  1. filtrationfiltered through a pad of silica gel (10 g) with diethyl ether (5 mL)
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 1% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4d7f8e2f508e41be87633e78b3f12b24
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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