Sodium hydride → HCID 53812906, compound

HRID 2396863Notes

Reaction equation

HRID 2396863 reaction equation
[F:1][C:2]1[C:3]([CH3:16])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](C(O)=O)=[C:5]2[O:14][CH3:15].[H-].[Na+].[CH3:19][C@@H:20]1[CH2:22][O:21]1>C1(OC2C=CC=CC=2)C=CC=CC=1.O1CCCC1>[F:1][C:2]1[C:3]([CH3:16])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:19][C@H:20]([OH:21])[CH3:22])[CH:6]=[C:5]2[O:14][CH3:15]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 146261(R)-1,2-EpoxypropaneHCID 18986241HCID 18986241, compound

Product 1

HCID 53812906HCID 53812906, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 7583Diphenyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1.98 g of 5-fluoro-3-methoxy-4-methylindole-2-carboxylic acid in 16 ml of diphenyl ether was stirred at 260° for 0.5 hour and, after cooling to 0°, diluted with 44 ml of tetrahydrofuran. 0.33 g of sodium hydride dispersion was added and the mixture was stirred for one hour. Subsequently, 1 ml of (R)-methyloxirane was added and the reaction mixture was stirred at room temperature for 90 hours. The mixture was extracted with diethyl ether, water and saturated sodium chloride solution and the organic phase was dried over sodium surfate. The solvent was removed and the residue was chromatographed over 120 g of silica gel with toluene and toluene-ethyl acetate (9:1). 1.69 g (80%) of (R)-1-(5-fluoro-3-methoxy-4-methylindol-1-yl)-propan-2-ol were obtained as a pale brown oil.

Workup

  1. temperatureafter cooling to 0°
  2. stirringthe mixture was stirred for one hour
  3. stirringthe reaction mixture was stirred at room temperature for 90 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 surfate
  6. customThe solvent was removed
  7. customthe residue was chromatographed over 120 g of silica gel with toluene and toluene-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-94cef2a4035c4473ad7e086d7608eade
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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