反应详情

This 3.21 g of 2-bromo-3-hexyl-5,5-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene were placed in 30 ml of abs. tetrahydrofuran under Ar and treated at -78° with 6.75 ml of 1.55M nBuLi (hexane) (1.1 eq.). The metal/halogen exchange was followed by gas chromatography (GC). After 40 min., a large excess of CO2 gas was introduced and the cooling bath was removed. After 10 min., the mixture was poured on to ice/NH4Cl solution, extracted with diethyl ether, washed with H2O, dried over Na2SO4 and the solvent was removed in a vacuum. Flash chromatography on SiO2 (hexane/ethyl acetate=8/2) yielded 2.26 g of 3-hexyl-5,5-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene-2-carboxylic acid as white crystals of m.p. 74°-75°.

1. customthe cooling bath was removed
2. waitAfter 10 min.
3. additionthe mixture was poured on to ice/NH4Cl solution
4. extractionextracted with diethyl ether
5. washwashed with H2O
6. dry with materialdried over Na2SO4
7. customthe solvent was removed in a vacuum