Water → 1H-Indole-1-ethanol, 5-chloro-6-fluoro-α-methyl-, (R)-

HRID 2396853Notes

Reaction equation

HRID 2396853 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[F:13])[NH:9][CH:8]=[CH:7]2.[CH3:14][C@@H:15]1[CH2:17][O:16]1.O>O1CCCC1.CCOCC>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[F:13])[N:9]([CH2:14][C@H:15]([OH:16])[CH3:17])[CH:8]=[CH:7]2

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 146261(R)-1,2-EpoxypropaneHCID 27736475-chloro-6-fluoro-1H-indole

Product 1

HCID 537885991H-Indole-1-ethanol, 5-chloro-6-fluoro-α-methyl-, (R)-Yield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 128 mg of sodium hydride dispersion in 8 ml of tetrahydrofuran was treated with 0.5 7 g of 5-chloro-6-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.48 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removing the solvent the residue was chromatographed over 25 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.59 g (77%) of (R)-1-(5-chloro-6-fluoro-indol-1-yl)-propan-2-ol as beige crystals with m.p. 108°-110°.

Workup

  1. stirringwas stirred at room temperature for 48 hours
  2. washwashed with water and with saturated sodium chloride solution
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. customAfter removing the solvent the residue
  5. customwas chromatographed over 25 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-65ff0a26b5ae4fd68dc085ecf1ca3e51
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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