Diethyl Ether → 3-[3-(4-Fluorophenyl)bicyclo[3.2.1]oct-2-en-2-yl]-propenal

HRID 982060Notes

Reaction equation

[Li+].CC([N-]C(C)C)C.C(=NC1CCCCC1)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH2:31][CH:30]3[CH2:32][CH:27]([CH2:28][CH2:29]3)[C:26]=2[CH:33]=O)=[CH:21][CH:20]=1.CC[O:37][CH2:38][CH3:39]>O>[F:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH2:31][CH:30]3[CH2:32][CH:27]([CH2:28][CH2:29]3)[C:26]=2[CH:33]=[CH:39][CH:38]=[O:37])=[CH:23][CH:24]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a 0°-5° C. solution of LDA (26.5 mmoles) in 25 ml anhydrous ether was added ethylidenecyclohexylamine (Org. Syn. 50 66) (3.32 g, 26.5 mmoles) in 25 ml anhydrous ether. The solution was stirred for 10 minutes, cooled to -70° C. and 3-(4-fluorophenyl)bicyclo[3.2.1]oct-2-ene-2-carboxaldehyde (5.55 g, 24.1 mmoles) in 25 ml ether was added. The solution was stirred for 60 minutes, warmed to 0°-5° C., stirred for 90 minutes and diluted with water. The organic layer was washed with water and brine and dried (MgSO4). Removal of the volatiles in vacuo provided a residue which was purified by HPLC using 3% ethyl acetate in hexanes as the eluent. Concentration in vacuo of the product rich fractions provided 2.53 g of the product as an orange oil.

Workup

stirringThe solution was stirred for 60 minutes
temperaturewarmed to 0°-5° C.
stirringstirred for 90 minutes
washThe organic layer was washed with water and brine
dry with materialdried (MgSO4)
customRemoval of the volatiles in vacuo
customprovided a residue which
customwas purified by HPLC
concentrationConcentration in vacuo of the product rich fractions

Sources & evidence

ORD record: ord-ddfcf004e18c4ab9bf9130556ca15ff7
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04994494

Reaction notes

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