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

HRID 500534노트

반응식

HRID 500534 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-de67189d8d0e4d78ae7e8bd16769225c
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772235B2

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