Tetrahydrofuran → HCID 57558474, compound

HRID 1723976Notes

Reaction equation

HRID 1723976 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12](=[O:26])[CH2:13][C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[CH:8]=2)[O:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1C[O:41]CC1>>[CH3:1][C:2]1([CH3:27])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12](=[O:26])[CH:13]([OH:41])[C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[CH:8]=2)[O:3]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 2724254Sodium bis(trimethylsilyl)amideHCID 9799516HCID 9799516, compound

Product 1

HCID 57558474HCID 57558474, compound

Procedure

The 1-(2,2-dimethyl-chroman-6-yl)-2-(3,4,5-trimethoxy-phenyl)-ethanone (184.1 mg, 0.5 mmol) dissolved in THF (3 mL) is added dropwise to a stirring cold (−78° C.) solution of NaHMDS (0.6 mL, 1.0M in THF) in THF (3 mL). The resulting reaction mixture is stirred for 30 minutes before (+/−)-camphoryl-sulfonyloxaziridine (187 mg, 0.75 mmol) in THF (3 mL) is added dropwise. After 15 minutes the reaction mixture is quenched with sat. NH4I (aqueous) solution (3 mL) and diluted with diethyl ether. The mixture is allowed to warm up to room temperature. The aqueous layer is extracted with diethyl ether. Combined organic layers are washed with water, brine, dried over sodium sulfate, filtered, and concentrated. Crude 1-(2,2-dimethyl-2H-chromen-6-yl)-2-hydroxy-2-(3,4,5-trimethoxy-phenyl)-ethanone is purified using silica gel chromatography.

Workup

  1. customThe resulting reaction mixture
  2. additionis added dropwise
  3. customAfter 15 minutes the reaction mixture is quenched with sat. NH4I (aqueous) solution (3 mL)
  4. additiondiluted with diethyl ether
  5. extractionThe aqueous layer is extracted with diethyl ether
  6. washCombined organic layers are washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customCrude 1-(2,2-dimethyl-2H-chromen-6-yl)-2-hydroxy-2-(3,4,5-trimethoxy-phenyl)-ethanone is purified

Sources & evidence

ORD record
ord-3f2638c54ba745fc9d8ee8fcfda22db4
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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