Tetrabutylammonium Fluoride → 2-(2-hydroxy-ethyl)-1H-indole-5-carbaldehyde

HRID 591681노트

반응식

HRID 591681 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9]C(=O)C)=[C:5]([C:13]#[C:14][CH2:15][CH2:16][OH:17])[CH:4]=1)=[O:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:17][CH2:16][CH2:15][C:14]1[NH:9][C:6]2[C:5]([CH:13]=1)=[CH:4][C:3]([CH:1]=[O:2])=[CH:8][CH:7]=2

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 86662028N-[4-formyl-2-(4-hydroxy-but-1-ynyl)-phenyl]-acetamide

생성물 1

HCID 866620292-(2-hydroxy-ethyl)-1H-indole-5-carbaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of N-[4-formyl-2-(4-hydroxy-but-1-ynyl)-phenyl]-acetamide (0.85 g, approximately 2.80 mmol) in THF (20 mL) was added a THF solution of TBAF (6.0 mL, 6.0 mmol) and the reaction mixture was stirred at reflux for 36 hours under nitrogen and cooled to room temperature. Solvent was evaporated and the residue was taken in ethyl acetate (200 mL). The organic phase was washed with water (2×100 mL), brine (100 mL) and dried over anhydrous Na2SO4. Solvent was evaporated; crude compound was purified by simpliflash system (50% ethyl acetate in hexanes as eluent) to give 2-(2-hydroxy-ethyl)-1H-indole-5-carbaldehyde as yellow solid. Yield: 0.31 g (58% for two steps).

후처리

  1. temperatureat reflux for 36 hours under nitrogen
  2. customSolvent was evaporated
  3. washThe organic phase was washed with water (2×100 mL), brine (100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customSolvent was evaporated
  6. customcrude compound was purified by simpliflash system (50% ethyl acetate in hexanes as eluent)

출처 및 근거

ORD 기록
ord-4f887398599b4bab86ed961f3c74013c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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