Ethyl 6-chloroindole-2-carboxylate → (6-Chloro-1H-indol-2-yl)methanol

HRID 1866029Notes

Reaction equation

HRID 1866029 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([Cl:15])[CH:9]=2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[Cl:15][C:10]1[CH:9]=[C:8]2[C:13]([CH:14]=[C:6]([CH2:4][OH:3])[NH:7]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7015027Ethyl 6-chloroindole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 16115151(6-Chloro-1H-indol-2-yl)methanolYield 101%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2.00 g (8.94 mmol) 6-chlorindole-2-carboxylic acid ethyl ester in 50 ml diethyl ether were added 0.475 g (12.5 mmol) lithium aluminum hydride at 0° C. The reaction mixture was heated at reflux for 45 min and quenched by consecutive addition of 10 ml water, 10 ml aqueous 2 M sodium hydroxide solution and 10 ml water at 0° C. The aqueous layer was extracted with tert-butyl methyl ether (3×100 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the crude title compound (1.64 g; 100%) as a white solid. MS m/e (%): 180 (M−H+, 100).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 45 min
  3. customquenched by consecutive addition of 10 ml water, 10 ml aqueous 2 M sodium hydroxide solution and 10 ml water at 0° C
  4. extractionThe aqueous layer was extracted with tert-butyl methyl ether (3×100 ml)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5882cb48e9f04ca6a5ddaf0208878dec
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

Loading…