Boron trifluoride → 4,4,8-Trimethyl-9-methylene-bicyclo[3.3.1]nonan-6-one

HRID 903303Notes

Reaction equation

HRID 903303 reaction equation
[CH3:1][C:2]1[CH:3]([C:10](=[O:14])/[CH:11]=[CH:12]/[CH3:13])[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH:7]=1.B(F)(F)F>C1C=CC=CC=1.CCOCC>[CH3:9][C:4]1([CH3:8])[CH:3]2[C:2](=[CH2:1])[CH:7]([CH:12]([CH3:13])[CH2:11][C:10]2=[O:14])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 6356Boron trifluorideHCID 5366077(E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one

Product 1

HCID 233380624,4,8-Trimethyl-9-methylene-bicyclo[3.3.1]nonan-6-one

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,6,6-trimethyl-1-crotonoyl-2-cyclohexene (1.0 g.) in a mixture of benzene and ether (10 ml.) was heated at ca. 80° in the presence of a catalytic amount of a saturated solution of BF3 in ether. The course of the reaction was followed by v.p.c. analysis. Three hours were usually necessary for converting the starting material into the bicyclic compound.

Workup

  1. customThree hours

Sources & evidence

ORD record
ord-96953c90447b47a983014c63a1cff3e8
Source dataset
uspto-grants-1980_10
Patent number
US04226892

Reaction notes

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