Ammonia → (2-Cyclohexen-1-yloxy)(trimethyl)silane

HRID 1278411Notes

Reaction equation

HRID 1278411 reaction equation
FC(F)(F)S([O:6][Si:7]([CH3:10])([CH3:9])[CH3:8])(=O)=O.O1[CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]12.C1CCN2C(=NCCC2)CC1.N>C1C=CC=CC=1>[CH3:8][Si:7]([CH3:10])([CH3:9])[O:6][CH:19]1[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 9246Cyclohexene oxideHCID 65367Trimethylsilyl triflateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 521533(2-Cyclohexen-1-yloxy)(trimethyl)silaneYield 87%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Into a solution of 2.26 g (0.0102 mole) of trimethylsilyl trifluoromethanesulfonate in 20 ml of benzene was added dropwise a mixed solution of 1.06 g (0.0107 mole) of 1,2-epoxycyclohexane and 2 ml of DBU in 5 ml of benzene at room temperature under an atmosphere of argon. After further agitation for 20 hours at room temperature, the reaction mixture was subjected to column chromatography with silica gel treated with ammonia as the adsorbent. Subsequent distillation of a chromatographic fraction gave 1.51 g of 3-trimethylsiloxycyclohexene boiling at 50° to 60° C. under a pressure of 50 mmHg. The yield was about 87% of the calculated value.

Workup

  1. distillationSubsequent distillation of a chromatographic fraction

Sources & evidence

ORD record
ord-56820b0074dd4bba966cf18f924b46b5
Source dataset
uspto-grants-1981_07
Patent number
US04281148

Reaction notes

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