Toluene → 3-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol

HRID 1941725노트

반응식

HRID 1941725 반응식
C1(C)C=CC=CC=1.[CH2:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]3[CH2:28][CH2:27][CH:26]([CH:29]4[CH2:34][CH2:33][CH:32]([CH2:35][CH2:36][CH3:37])[CH2:31][CH2:30]4)[O:25][C:24]3=[O:38])=[C:19]([F:39])[C:18]=2[F:40])=[C:13]([F:41])[C:12]=1[F:42])[CH3:9].[H-].C([Al+]CC(C)C)C(C)C>C(O)=O>[CH2:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]3[CH2:28][CH2:27][CH:26]([CH:29]4[CH2:30][CH2:31][CH:32]([CH2:35][CH2:36][CH3:37])[CH2:33][CH2:34]4)[O:25][CH:24]3[OH:38])=[C:19]([F:39])[C:18]=2[F:40])=[C:13]([F:41])[C:12]=1[F:42])[CH3:9]

참가 물질

5

반응물 3

HCID 1140Toluene2회HCID 21225700DiisobutylaluminumhydrideHCID 585356163-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-one

생성물 1

HCID 585356523-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol수율 99%

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

Toluene (20 ml) was added to 3-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-one (11) (2.35 g) prepared in the ninth step. A toluene solution of diisobutylaluminum hydride (0.99 M; 9.6 ml) was added dropwise at −50° C. or lower, and the stirring was continued for 3 hours. The reaction mixture was poured into a 10% aqueous solution of formic acid (50 ml) to give two layers. The water layer was extracted with toluene (20 ml) twice and the combined organic layer was washed with water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to leave 3-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol (12) (2.29 g) in 99% yield.

후처리

  1. customprepared in the ninth step
  2. customto give two layers
  3. extractionThe water layer was extracted with toluene (20 ml) twice
  4. washthe combined organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-049b9a6afd59455d86d9e852754942a8
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389073B2

반응 노트

불러오는 중…