Water → HCID 228327, compound

HRID 1415720Notes

Reaction equation

HRID 1415720 reaction equation
[CH3:1][C@H:2]1[CH2:11][C:9](=[O:10])[C:5](=[C:6]([CH3:8])[CH3:7])[CH2:4][CH2:3]1.[CH3:12][Al](C)C.C[Si](Cl)(C)C.O>C1COCC1.C1(C)C=CC=CC=1>[C:6]([CH:5]1[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:11][C:9]1=[O:10])([CH3:12])([CH3:7])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 442495(+)-PulegoneHCID 16682925Trimethylaluminum

Product 1

HCID 228327HCID 228327, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.52 g (10 mmol) of pulegone (2-isopropylidene-5-methylcyclohexanone) and 14.3 mg (0.1 mmol) of CuBr in 10 ml of dry THF are introduced at room temperature. 9.5 ml (11 mmol) of 10% trimethylaluminum in toluene and 1.3 g (12 mmol) of trimethylsilyl chloride are added at 0° C. It is stirred for 5 more hours at room temperature, hydrolyzed with 5 ml of water and extracted twice with 30 ml of ether each, and the organic phases are combined. After the solvent is evaporated, the product is distilled at 10 torr and 120° C. in a bulb tube. 1.45 g (86% of theory) of 2-tert-butyl-5-methylcyclohexanone is obtained.

Workup

  1. extractionextracted twice with 30 ml of ether each, and the organic phases
  2. customAfter the solvent is evaporated
  3. distillationthe product is distilled at 10 torr and 120° C. in a bulb tube

Sources & evidence

ORD record
ord-eb1d085fd1194028a032845d3c1a7409
Source dataset
uspto-grants-1999_06
Patent number
US05908945

Reaction notes

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