Tetrabutylammonium Fluoride → 6-(4-hydroxy-cyclohex-1-enyl)-1-methyl-1H-indole-3-carboxylic acid methyl ester

HRID 1689777Notes

Reaction equation

HRID 1689777 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH2:19][CH2:18][CH:17]([O:20][Si](C(C)(C)C)(C)C)[CH2:16][CH:15]=3)=[CH:11][CH:12]=2)[N:7]([CH3:28])[CH:6]=1)=[O:4].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH:15]=3)=[CH:11][CH:12]=2)[N:7]([CH3:28])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66906357HCID 66906357, compound

Product 1

HCID 669063356-(4-hydroxy-cyclohex-1-enyl)-1-methyl-1H-indole-3-carboxylic acid methyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-1-methyl-1H-indole-3-carboxylic acid methyl ester (0.710 g, 1.78 mmol) in THF (10 mL) is treated with Bu4NF (2.22 mL, 1.0 M in THF). The mixture is stirred at room temperature for 5 h and concentrated under reduced pressure. The residue is purified by silica gel chromatography eluting with a gradient of 25-80% EtOAc/Hexanes to provide the 6-(4-hydroxy-cyclohex-1-enyl)-1-methyl-1H-indole-3-carboxylic acid methyl ester (0.320 g, 63%). MS m/z 286.3 (M+1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified by silica gel chromatography
  3. washeluting with a gradient of 25-80% EtOAc/Hexanes

Sources & evidence

ORD record
ord-7a13e407c65c46188475a3426c3dc3b5
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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