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

HRID 1086100노트

반응식

HRID 1086100 반응식
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[C:14]([CH:22]([F:24])[F:23])[CH2:15]P(=O)(OC)OC)=[CH:9][CH:8]=1.[CH:32]([CH:34]1[O:39][C:38](C)(C)[O:37][CH:36]([CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:35]1)=O>O1CCCC1>[F:23][CH:22]([F:24])[C:14](=[C:13]([C:10]1[CH:9]=[CH:8][C:7]([F:6])=[CH:12][CH:11]=1)[C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1)[CH:15]=[CH:32][CH:34]1[O:39][CH2:38][O:37][CH:36]([CH2:42][C:43]([O:45][C:46]([CH3:47])([CH3:49])[CH3:48])=[O:44])[CH2:35]1

참가 물질

5

반응물 3

HCID 156146011,1-Dimethylethyl 6-formyl-2,2-dimethyl-1,3-dioxane-4-acetateHCID 54009116Dimethyl [3,3-bis(4-fluorophenyl)-2-difluoromethyl-2-propen-1-yl]phosphonateHCID 178418339Butyllithium

생성물 1

HCID 536982541,1-Dimethylethyl 6-[3-difluoromethyl-4,4-bis(4-fluorophenyl)-1,3-butadienyl]-1,3-dioxane-4-acetate수율 46.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Butyl lithium (1.04 mL of 2.5M solution, 2.6 mmol) was added to a solution of dimethyl [3,3-bis(4-fluorophenyl)-2-difluoromethyl-2-propen-1-yl]phosphonate (1.0 g, 2.6 mmol) in 10 mL of tetrahydrofuran at -78° C. After stirring for 30 minutes, 1,1-dimethylethyl 6-formyl-2,2-dimethyl-1,3-dioxane-4-acetate (0.82 g, 3.2 mmol) was added and the mixture stirred for 64 hrs. at room temperature. The mixture was quenched with saturated ammonium chloride solution and extracted with diethyl ether. The extracts were dried over magnesium sulfate and conentrated in vacuo. The residue was purified by chromatography on silica eluting with 5% ethyl acetate in hexane to give an oil. Crystallization from pentane gave 0.6 g of the title compound; m.p. =124°-125° C.

후처리

  1. stirringthe mixture stirred for 64 hrs
  2. customat room temperature
  3. customThe mixture was quenched with saturated ammonium chloride solution
  4. extractionextracted with diethyl ether
  5. dry with materialThe extracts were dried over magnesium sulfate
  6. customThe residue was purified by chromatography on silica eluting with 5% ethyl acetate in hexane
  7. customto give an oil
  8. customCrystallization from pentane

출처 및 근거

ORD 기록
ord-f6efdf4cc3df4b71b32c6117ddb89c79
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05011947

반응 노트

불러오는 중…