4-tert-Butylcyclohexanone → HCID 10911276, compound

HRID 2407606Notes

Reaction equation

HRID 2407606 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].[CH3:12][Si:13](C)([CH3:23])[CH2:14]C(C1C=CC=CC=1)=C.N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.CCN(CC)CC.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.ClCCl>[C:1]([CH:5]1[CH2:6][CH2:7][C:8]([O:11][Si:13]([CH3:23])([CH3:14])[CH3:12])=[CH:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 73924-tert-ButylcyclohexanoneHCID 8471TriethylamineHCID 157857Bis(trifluoromethane)sulfonimideHCID 516892Sodium BicarbonateHCID 10965317Silane, trimethyl(2-phenyl-2-propenyl)-

Product 1

HCID 10911276HCID 10911276, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21877217Toluene methylene chlorideSolvent3×

Procedure

A solution (2.0 ml) of the mixture of 4-tert-butylcyclohexanone (1b) (77.1 mg, 0.500 mmol, 0.250 M) and trimethyl(2-phenylallyl)silane (2d) (85.2 mg, 0.500 mmol, 0.250 M) in toluene/dichloromethane (1:1, volume ratio), solution (2.0 ml) of Tf2NH (1.41 mg, 5.00 μmol, 2.50 mM) in toluene/dichloromethane (1:1, volume ratio), and a solution (5.0 ml) of NEt3 (2.53 mg, 25.0 μmol, 5.00 mM) in toluene/dichloromethane (1:1, volume ratio) were used as solution A, solution B and solution C, respectively. The three kinds of solutions were each loaded in a gas tight syringe, and set on a syringe pump as shown in the above-mentioned schematic diagram. Using a microreactor (manufactured by Techno Applications Co., Ltd., COMET-X01) at room temperature, solution A and solution B were continuously supplied at a flow rate of 150 μl/min, and solution C was supplied at a flow rate of 300 μl/min. A micromixer was set at a place where solution A and solution B were mixed, and a micromixer was also set at a place where mixture A-B and solution C were mixed. A flask containing ice-cooled aqueous sodium hydrogen carbonate solution was set at the outlet of the reaction mixture, and the mixture of A, B and C was collected there. After completion of the reaction, the recovered product was extracted with hexane and the organic layer was dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give the object product, 4-tert-butyl-1-trimethylsilyloxy-1-cyclohexene (3b) (yield 90%). The time necessary for mixing solution A and solution B (calculated from distance between the two micromixers and flow rate) was 145 sec, and the time necessary for mixing mixture A-B and solution C (calculated from distance from the second micromixer to reaction mixture outlet and flow rate) was 40 sec.

Workup

  1. customeach loaded in a gas tight syringe
  2. customset on a syringe
  3. customat room temperature
  4. additionwere mixed
  5. additionwere mixed
  6. additionA flask containing ice-
  7. additionthe mixture of A, B and C
  8. customwas collected there
  9. customAfter completion of the reaction
  10. extractionthe recovered product was extracted with hexane
  11. dry with materialthe organic layer was dried over sodium sulfate
  12. filtrationAfter filtration
  13. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d4db9e99ddee442aa53fa37d5c6434d1
Source dataset
uspto-grants-2014_08
Patent number
US08809567B2

Reaction notes

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