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

HRID 1453802ノート

反応式

HRID 1453802 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

(1R)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethyl acetate (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 r.t. over night. Reducing the volume of the mixture in vacuo to about ½, 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=70:30, to give the title compound (40 g, 85%). 1H NMR: 7.73 (m, 1H), 7.63 (m, 1H), 7.38 (m, 2H), 6.57 (s, 1H), 5.07 (q, 1H), 2.44 (s, 1H), 1.59 (d, 3H).

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-b97e1fb0d44e4c33a47251d88b95c6bf
出典データセット
uspto-grants-2009_01
特許番号
US07476684B2

反応ノート

読み込み中…