Water → HCID 10633079, compound

HRID 2396835Notes

Reaction equation

HRID 2396835 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][C:5]=1[F:13].[CH3:14][C@H:15]1[CH2:17][O:16]1.O>O1CCCC1.CCOCC>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:14][C@@H:15]([OH:16])[CH3:17])=[CH:6][C:5]=1[F:13]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 146262(2S)-2-MethyloxiraneHCID 27736486-Chloro-5-fluoro-1H-indole

Product 1

HCID 10633079HCID 10633079, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.11 g of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.5 g of 6-chloro-5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.42 ml of (S)-methyloxirane the reaction mixture was stirred at room temperature for 85 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 removal of the solvent the residue was chromatographed over 25 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.54 g (79%) of (S)-1-(6-chloro-5-fluoro-indol-1-yl)-propan-2-ol as beige crystals (m.p. 99°-101°).

Workup

  1. stirringwas stirred at room temperature for 85 hours
  2. washwashed with water and with saturated sodium chloride solution
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. customAfter removal of the solvent the residue
  5. customwas chromatographed over 25 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-178833c39bb84295a9917ea309c27c82
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

Loading…