Sodium Hydroxide → Triphenylsulfonium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate

HRID 58518

反応式

HRID 58518 の反応式
C([O:3][C:4]([C:6]([F:28])([F:27])[CH:7]([O:14][C:15]([C:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])C.O1CCOCC1.[OH-].[Na+].[Cl-].[C:38]1([S+:44]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl.O>[C:17]12([C:15]([O:14][CH:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:6]([F:27])([F:28])[C:4]([O-:5])=[O:3])=[O:16])[CH2:24][CH:23]3[CH2:25][CH:19]([CH2:20][CH:21]([CH2:22]3)[CH2:26]1)[CH2:18]2.[C:51]1([S+:44]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 61343Triphenylsulfonium chlorideHCID 1179666922-Ethoxycarbonyl-2,2-difluoro-1-phenylethyl 1-adamantanecarboxylate

生成物 1

HCID 131737015Triphenylsulfonium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate収率 58%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

After stirring a mixed solution of 1-adamantane carboxylic acid 2-ethoxycarbonyl-2,2-difluoro-1-phenyl-ethyl ester (6.6 g) prepared in Synthesis Example 1-5, 1,4-dioxane (20 g) and 25% by mass of caustic soda (2.5 g) for 2 hours, water (30 g) was added to the reaction solution and washed with n-hexane to prepare an aqueous solution of sodium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate. An aqueous solution of triphenylsulfonium chloride (32 g) and methylene chloride (100 g) were added to the product, stirred for 30 minutes, and then an organic layer was isolated and washed with water, and thereafter was concentrated under reduced pressure. Methylisobutyl ketone was added to the concentrated solution, and concentrated again. Diisopropyl ether was added to the concentrated solution for crystallization, and a solid obtained was dried under reduced pressure to obtain a target compound, or triphenylsulfonium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate (5.5 g) as a white crystal (yield: 58%).

後処理

  1. washwashed with n-hexane
  2. customto prepare an aqueous solution of sodium 3-(adamantane-1-carbonyloxy)-2,2-difluoro-3-phenyl propionate
  3. customan organic layer was isolated
  4. washwashed with water
  5. concentrationwas concentrated under reduced pressure
  6. additionMethylisobutyl ketone was added to the concentrated solution
  7. concentrationconcentrated again
  8. additionDiisopropyl ether was added to the concentrated solution for crystallization
  9. customa solid obtained
  10. customwas dried under reduced pressure

出典と根拠

ORDレコード
ord-fe5ebfbe225e49188c545315d78d274f
出典データセット
uspto-grants-2016_09
特許番号
US09436083B2

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