Sodium Hydroxide → [1-(1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetic acid

HRID 1451535노트

반응식

HRID 1451535 반응식
[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][C:22]([O:24]C)=[O:23])[CH2:20][CH2:19]3)=[C:8]2[CH3:26])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.CCOCC.CCCCCC>[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][C:22]([OH:24])=[O:23])[CH2:20][CH2:19]3)=[C:8]2[CH3:26])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 53800337Methyl [1-(1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetate

생성물 1

HCID 19041685[1-(1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetic acid수율 78%

시약·촉매·용매 2

HCID 887Methanol용매HCID 21584099Diethylether hexane용매

실험 절차

To the methyl ester from Step 7 (1.63 g, 3.68 mmol) in 20 mL of methanol was added 5 mL of 2N NaOH, and the mixture was heated to reflux for 2 h then cooled. The reaction mixture was partitioned between ethyl acetate and 1M HCl. The organic layer was washed with brine, dried over MgSO4 and evaporated to give a solid. This material was swished twice in 15% ether/hexane to provide 1.23 g of the title compound.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. temperaturethen cooled
  4. customThe reaction mixture was partitioned between ethyl acetate and 1M HCl
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give a solid

출처 및 근거

ORD 기록
ord-2cfd5522bbad4582b830604fd9c9f0e7
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05604253

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