Water → 2-(4-Chloro-1H-indol-3-yl)ethanol

HRID 2306977Notes

Reaction equation

HRID 2306977 reaction equation
C([O:3][C:4](=O)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[Cl:16])[NH:9][CH:8]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1.CCOC(C)=O>[Cl:16][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[C:7]([CH2:5][CH2:4][OH:3])=[CH:8][NH:9]2

Participants

6

Reactant 3

HCID 962WaterHCID 12230410HCID 12230410, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 122304112-(4-Chloro-1H-indol-3-yl)ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-chloro-3-(1H)-indoleglyoxylic acid ethyl ester (7.04 g, 30.0 mmol) in dry THF (0.4 L), at 0° C. under argon was added portionwise LiAlH4 (5.4 g, 135.2 mmol). The suspension was stirred at 0° C. for 20 min and at reflux for 3.5 h, cooled to 0° C., and water (17.6 mL) was added. It was stirred for 10 min, and then diluted with EtOAc. The reaction mixture was filtered. The solid was washed with EtOAc. The combined EtOAc portions were washed with water and brine, dried, filtered, and concentrated to give the title compound: TLC Rf=0.38 (9:1 CH2Cl2/Me2CO); MS (ESI−) m/z 194.0; 13C NMR (75 MHz, CDCl3) δ 138.02, 126.42, 124.21, 124.12, 122.70, 120.61, 112.63, 110.06, 63.59, 29.78.

Workup

  1. temperatureat reflux for 3.5 h
  2. temperaturecooled to 0° C.
  3. stirringIt was stirred for 10 min
  4. filtrationThe reaction mixture was filtered
  5. washThe solid was washed with EtOAc
  6. washThe combined EtOAc portions were washed with water and brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8a013b97ba6641ae94386218ab0e284f
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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