Sodium hydride → HCID 54534806, compound

HRID 2396847Notes

Reaction equation

HRID 2396847 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[NH:7][C:6](C(O)=O)=[CH:5]2.[H-].[Na+].[CH3:20][C@@H:21]1[CH2:23][O:22]1>C1(OC2C=CC=CC=2)C=CC=CC=1.O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([F:12])([F:13])[F:14])[N:7]([CH2:20][C@H:21]([OH:22])[CH3:23])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 146261(R)-1,2-EpoxypropaneHCID 18986252HCID 18986252, compound

Product 1

HCID 54534806HCID 54534806, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 7583Diphenyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.75 g of 5-fluoro-6-trifluoromethylindole-2-carboxylic acid in 16 ml of diphenyl ether was stirred at 260° for 4 hours and, after cooling to 0°, diluted with 16 ml of tetrahydrofuran. 113 mg of sodium hydride dispersion were added and the mixture was stirred for 1 hour. Subsequently, 0.43 ml of (R)-methyloxirane was added and the reaction mixture was stirred at room temperature for 60 hours. The mixture was extracted with diethyl ether, water and saturated sodium chloride solution and the organic phase was dried over sodium sulfate. The solvent was removed and the residue was chromatographed over 40 g of silica gel with hexane-toluene (1:1) and subsequently with toluene-ethyl acetate (15:1). There was obtained 0.15 g (18.9%) of (R)-1-(5-fluoro-6-trifluoromethyl-indol-1-yl)-propan-2-ol as light brown crystals.

Workup

  1. temperatureafter cooling to 0°
  2. stirringthe mixture was stirred for 1 hour
  3. stirringthe reaction mixture was stirred at room temperature for 60 hours
  4. extractionThe mixture was extracted with diethyl ether, water and saturated sodium chloride solution
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. customThe solvent was removed
  7. customthe residue was chromatographed over 40 g of silica gel with hexane-toluene (1:1) and subsequently with toluene-ethyl acetate (15:1)

Sources & evidence

ORD record
ord-c947b34c580c470bab0d1ed9b0d44b64
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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