1,1-Dimethylethyl 6-formyl-2,2-dimethyl-1,3-dioxane-4-acetate → 1,1-Dimethylethyl 6-[4,4-bis(4-fluorophenyl)-3-trifluoromethyl-1,3-butadienyl]-1,3-dioxane-4-acetate

HRID 1086102Notes

Reaction equation

HRID 1086102 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[C:14]([C:22]([F:25])([F:24])[F:23])[CH2:15]P(=O)(OC)OC)=[CH:9][CH:8]=1.[CH:33]([CH:35]1[O:40][C:39](C)(C)[O:38][CH:37]([CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:36]1)=O>O1CCCC1>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C:13]([C:10]2[CH:9]=[CH:8][C:7]([F:6])=[CH:12][CH:11]=2)=[C:14]([C:22]([F:23])([F:25])[F:24])[CH:15]=[CH:33][CH:35]2[O:40][CH2:39][O:38][CH:37]([CH2:43][C:44]([O:46][C:47]([CH3:48])([CH3:50])[CH3:49])=[O:45])[CH2:36]2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 156146011,1-Dimethylethyl 6-formyl-2,2-dimethyl-1,3-dioxane-4-acetateHCID 53881730Dimethyl [3,3-bis(4-fluorophenyl)-2-trifluoromethyl-2-propen-1-yl]phosphonateHCID 178418339Butyllithium

Product 1

HCID 540852831,1-Dimethylethyl 6-[4,4-bis(4-fluorophenyl)-3-trifluoromethyl-1,3-butadienyl]-1,3-dioxane-4-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Butyl lithium(1.2 mL of 2.5M solution, 3.0 mmol) was added to a solution of dimethyl [3,3-bis(4-fluorophenyl)-2-trifluoromethyl-2-propen-1-yl]phosphonate in 20 mL tetrahydrofuran at -70° C. followed by immediate addition of 1,1-dimethylethyl 6-formyl-2,2-dimethyl-1,3-dioxane-4-acetate (0.9 g, 3.6 mmol). The solution was allowed to gradually warm to room temperature and then stirred for 14 hours. The reaction was quenched with saturated ammonium chloride solution 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 10% ethyl acetate in hexane to give 0.7 g of the title compound as an oil. MS(CI): m/e =538 for M+ of C29H31F4O4.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride solution
  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 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1bfc4fbd8eed4c35a75ff7d2319e4559
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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