Lithium hydroxide, monohydrate → (R)-1-[5-(3-chloro-phenyl)-isoxazol-3-yl]-ethanol

HRID 500534ノート

反応式

HRID 500534 の反応式
C([O:4][C@@H:5]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[O:9][N:8]=1)[CH3:6])(=O)C.O.[OH-].[Li+]>C1COCC1.O>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[O:9][N:8]=[C:7]([C@H:5]([OH:4])[CH3:6])[CH:11]=2)[CH:17]=[CH:16][CH:15]=1

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 44605723(1R)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethyl acetate

生成物 1

HCID 46701926(R)-1-[5-(3-chloro-phenyl)-isoxazol-3-yl]-ethanol収率 85%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

The title compound of Example 16.1 (56 g, 211 mmol) and lithium hydroxide monohydrate (10.6 g, 253 mmol) were mixed with THF/Water (7/5, 1.2 L) and stirred at RT over night. Reducing the volume of the mixture in vacuo to about half, followed by dilution with brine, extraction with ether and then drying over MgSO4 and in vacuo concentration gave crude product. The crude product was purified by flash column chromatography on silica using heptane/EtOAc (7:3) to give the title compound (40 g, 85%).

後処理

  1. extractionfollowed by dilution with brine, extraction with ether
  2. dry with materialdrying over MgSO4 and in vacuo concentration
  3. customgave crude product
  4. customThe crude product was purified by flash column chromatography on silica

出典と根拠

ORDレコード
ord-de67189d8d0e4d78ae7e8bd16769225c
出典データセット
uspto-grants-2010_08
特許番号
US07772235B2

反応ノート

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