Methanol → 5-[2,4-Bis(benzyloxy)-5-chlorophenyl]-isoxazole-3-carboxylic acid

HRID 389934노트

반응식

HRID 389934 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[O:28][N:27]=[C:26]([C:29]([O:31]CC)=[O:30])[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[Li+].[OH-]>O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[O:28][N:27]=[C:26]([C:29]([OH:31])=[O:30])[CH:25]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 24774040Ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylate

생성물 1

HCID 670835065-[2,4-Bis(benzyloxy)-5-chlorophenyl]-isoxazole-3-carboxylic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of ethyl 5-(2,4-bis(benzyloxy)-5-chlorophenyl)isoxazole-3-carboxylate (200 mg, 0.43 mmol), methanol (10 ml), water (6-7 ml), and LiOH (16 mg, 0.65 mmol) was allowed to stand at 50-60° C. for 24 h. The solution was concentrated under vacuo to remove methanol, and the remaining aqueous solution was extracted with Et2O to remove traces of unreacted starting material. The aqueous solution was acidified with 1 M HCl and extracted with three portions of AcOEt. The combined organic extracts were washed with saturated aqueous sodium chloride and dried over sodium sulfate. Removal of the solvent under reduced pressure afforded a residue, which was chromatographed on silica gel (DCM/methanol: 9/1).

후처리

  1. concentrationThe solution was concentrated under vacuo
  2. customto remove methanol
  3. extractionthe remaining aqueous solution was extracted with Et2O
  4. customto remove traces
  5. extractionextracted with three portions of AcOEt
  6. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customRemoval of the solvent under reduced pressure
  9. customafforded a residue, which
  10. customwas chromatographed on silica gel (DCM/methanol: 9/1)

출처 및 근거

ORD 기록
ord-bcc4e13204e74a96a6176b2e9e70084c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383616B2

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