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

HRID 1356291Notes

Reaction equation

HRID 1356291 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-91fed09085bb4c59990283926375ae66
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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