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

HRID 1941725ノート

反応式

HRID 1941725 の反応式
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]

参加物

5

反応物 3

HCID 1140Toluene2 回HCID 21225700DiisobutylaluminumhydrideHCID 585356163-(4'-Ethoxy-2,2',3,3'-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-049b9a6afd59455d86d9e852754942a8
出典データセット
uspto-grants-2013_03
特許番号
US08389073B2

反応ノート

読み込み中…