Water → HCID 53854007, compound

HRID 2396862Notes

Reaction equation

HRID 2396862 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:13])=[CH:9][NH:10]2)=[CH:6][C:5]=1[F:14].[CH3:15][C@@H:16]1[CH2:18][O:17]1.O>O1CCCC1.CCOCC>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:13])=[CH:9][N:10]2[CH2:15][C@H:16]([OH:17])[CH3:18])=[CH:6][C:5]=1[F:14]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 146261(R)-1,2-EpoxypropaneHCID 189862576-Chloro-5-fluoro-3-methyl-1H-indole

Product 1

HCID 53854007HCID 53854007, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.07 g of sodium hydride dispersion in 10 ml of tetrahydrofuran was treated with 0.33 g of 6-chloro-5-fluoro-3-methylindole at 0° and stirred as this temperature for 1 hour. After the addition of 0.19 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 17 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 20 g of silica gel with toluene-ethyl acetate (9:1). 0.22 g (50%) of (R)-1-(6-chloro-5-fluoro-3-methylindol-1-yl)-propan-2-ol was obtained as a yellow oil.

Workup

  1. stirringwas stirred at room temperature for 17 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 20 g of silica gel with toluene-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-10b668d11e514842adbcadb107e6b55c
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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