Water → (RS)-1-(7-chloro-6-fluoro-indol-1-yl)-propan-2-ol

HRID 2396854Notes

Reaction equation

HRID 2396854 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([F:13])=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.[CH3:14][CH:15]1[CH2:17][O:16]1.O>O1CCCC1.CCOCC>[Cl:3][C:4]1[C:5]([F:13])=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([CH2:14][CH:15]([OH:16])[CH3:17])[CH:10]=[CH:9]2

Participants

7

Reactant 4

HCID 962WaterHCID 6378Propylene OxideHCID 24758Sodium hydrideHCID 189862317-chloro-6-fluoro-1H-indole

Product 1

HCID 18986243(RS)-1-(7-chloro-6-fluoro-indol-1-yl)-propan-2-olYield 77.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 45 mg of sodium hydride dispersion in 10 ml of tetrahydrofuran was treated with 0.2 g of 7-chloro-6-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.17 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 4 days 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 15 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.21 g (77.8%) of (RS)-1-(7-chloro-6-fluoro-indol-1-yl)-propan-2-ol as white crystals with m.p. 85°-87°.

Workup

  1. stirringwas stirred at room temperature for 4 days
  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 15 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-814d1845e9ca4fe8b02efacddf911f67
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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