Tetrabutylammonium Fluoride → tert-Butyl (6-hydroxy-1H-indol-1-yl)acetate

HRID 915383노트

반응식

HRID 915383 반응식
[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][Si](C(C)(C)C)(C)C)[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 69279688[6-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester

생성물 1

HCID 69283069tert-Butyl (6-hydroxy-1H-indol-1-yl)acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To an ice cooled solution of [6-(tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester (4.2 g, 11.6 mmol) in THF (24 ml) was added a 1 M solution of tetrabutylammonium fluoride in THF (11.6 ml, 11.6 mmol) within 15 min. The reaction mixture was stirred for 1 h at ambient temperature, poured onto 1 N HCl/ice water 1/1 and extracted two times with ethyl acetate. The combined organic layers were washed with brine/ice water 1/1 and dried over sodium sulfate. The solvent was removed under reduced pressure to give 3.4 g (quant.) of the title compound as brown oil which was used in the next step without further purification.

후처리

  1. extractionextracted two times with ethyl acetate
  2. washThe combined organic layers were washed with brine/ice water 1/1
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-9a7e6afa06ff46548ad4348a1e90157e
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265149B2

반응 노트

불러오는 중…