Water → HCID 10822377, compound

HRID 2396842Notes

Reaction equation

HRID 2396842 reaction equation
[H-].[Na+].[F: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>[F: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 27787325,6-Difluoro-1H-indole

Product 1

HCID 10822377HCID 10822377, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.12 g of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.5 g of 5,6-difluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.46 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 60 hours and subsequently treated with water. The mixture was diluted with ether, washed twice 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 35 g of silica gel with toluene-ethyl acetate (19:1). 0.46 g (66.5%) of (R)-1-(5,6-difluoro-indol-1-yl)-propan-2-ol was obtained as yellowish crystals with m.p. 114°-116°.

Workup

  1. stirringwas stirred at room temperature for 60 hours
  2. washwashed twice 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 35 g of silica gel with toluene-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-df95993637f84beab6e236757dfa1e23
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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