Dimethylformamide → HCID 70246679, compound

HRID 1978905Notes

Reaction equation

HRID 1978905 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C@:6]([CH3:18])([C:14]([F:17])([F:16])[F:15])[O:5]1.[CH3:19]N(C=O)C>>[CH3:19][O:3][CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C@:6]([CH3:18])([C:14]([F:15])([F:17])[F:16])[O:5]1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 70246728HCID 70246728, compound

Product 1

HCID 70246679HCID 70246679, compoundYield 98%

Procedure

To a stirred mixture of sodium hydride (3.47 g, 0.145 mol) in DMF (50 mL) was added (1R)-hydroxy-1-methyl-1-trifluoromethylisochroman (28.0 g, 0.121 mol) solution in DMF (370 mL) at 0° C., then the mixture was stirred at room temperature for 1 hr. The reaction mixture was quenched with water and diluted with saturated aqueous ammonium chloride. This was extracted with ethyl acetate-toluene (4:1). The organic fraction was washed with water and brine, and dried over magnesium sulfate. The solvent was removed in vacuo, the residue was purified by column chromatography on silica-gel eluted with hexane and ethyl acetate (40:1) to give the title compound as a colorless oil (29.1 g, 98%). The 1H-NMR spectra of this material was identical with that of racemate.

Workup

  1. customThe reaction mixture was quenched with water
  2. additiondiluted with saturated aqueous ammonium chloride
  3. extractionThis was extracted with ethyl acetate-toluene (4:1)
  4. washThe organic fraction was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by column chromatography on silica-gel
  8. washeluted with hexane and ethyl acetate (40:1)

Sources & evidence

ORD record
ord-a45c1ce2c15247569c0ff20b1139cc60
Source dataset
uspto-grants-2001_05
Patent number
US06239147B1

Reaction notes

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