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

HRID 591681ノート

反応式

HRID 591681 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4f887398599b4bab86ed961f3c74013c
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

反応ノート

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