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

HRID 591681Notes

Reaction equation

HRID 591681 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-4f887398599b4bab86ed961f3c74013c
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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