Chlorotrimethylsilane → Cyclohexene, 1-((trimethylsilyl)oxy)-

HRID 22059Notes

Reaction equation

HRID 22059 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][Si:9]([CH3:12])([CH3:11])Cl>C1COCC1.C[N-]C1C=CC=CC=1.C1([Mn+])C=CC=CC=1>[CH3:8][Si:9]([CH3:12])([CH3:11])[O:7][C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 2

HCID 6397Chlorotrimethylsilane2×HCID 7967Cyclohexanone

Product 1

HCID 81161Cyclohexene, 1-((trimethylsilyl)oxy)-Yield 59%

Reagents, catalysts & solvents 2

HCID 178482129HCID 178482129, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

- In another experiment, an enolate is prepared by the reaction of 100 mmol of phenylmanganese N-methyl-N-phenylamide: ##STR11## with 100 mmol of cyclohexanone in 200 ml of THF at 20° C. for 1 hour: ##STR12## 100 mmol of trimethylchlorosilane, ClSiMe3, are added to the resulting solution at 20° C. and the mixture is stirred for 30 minutes to produce the following reaction: ##STR13## 1-Trimethylsilyloxycyclohexene is obtained with a yield of 59%, compared with 77% for procedure A.

Workup

  1. customto produce
  2. customthe following reaction

Sources & evidence

ORD record
ord-4fae0e090ce045e89c782eaa665d0d49
Source dataset
uspto-grants-1995_06
Patent number
US05426201

Reaction notes

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