Tetrahydrofuran → HCID 86744757, compound

HRID 1086083Notes

Reaction equation

HRID 1086083 reaction equation
[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[C:20]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:21]=[CH:22][CH:23]=[O:24])=[CH:15][CH:14]=1.[O:36]1CCCC1>>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)=[C:20]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:21]=[CH:22][CH:23]([OH:24])[CH2:5][CH2:3][C:2](=[O:36])[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 15538Tert-butyl acetoacetateHCID 53866743HCID 53866743, compound

Product 1

HCID 86744757HCID 86744757, compound

Procedure

The dianion of 1,1-dimethylethyl acetoacetate (9.1 mL of 1M solution, 9.1 mmol) was added to a solution of 5,5-bis-(4-fluorophenyl)-4-(1,1-dimethylethyl)-2,4-pentadienal in 30 mL of tetrahydrofuran at -60° C. The solution was quenched with 2N hydrochloric acid and the mixture extracted with diethyl ether. The extracts were dried and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 0.5% methanol in methylene chloride to give 1.3 g of the title compound; m.p. =95°-97° C.

Workup

  1. customThe solution was quenched with 2N hydrochloric acid
  2. extractionthe mixture extracted with diethyl ether
  3. customThe extracts were dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica eluting with 0.5% methanol in methylene chloride

Sources & evidence

ORD record
ord-22455198e5134ad9805c806810ea3191
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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