Hydrochloric Acid → HCID 19822174, compound

HRID 1030405Notes

Reaction equation

HRID 1030405 reaction equation
[BH4-].[Na+].CO.[C:5]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[C:19]([CH3:26])([CH3:25])[CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[O:15][C:14]([CH3:38])([CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1)[CH2:13][C:12]2=[O:39])(=[O:7])[CH3:6].Cl>C1C=CC=CC=1>[C:5]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[C:19]([CH3:26])([CH3:25])[CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[O:15][C:14]([CH3:38])([CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1)[CH2:13][CH:12]2[OH:39])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 19822204HCID 19822204, compound

Product 1

HCID 19822174HCID 19822174, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1 g of sodium borohydride was added, whilst ice-cooling, to a mixture of 100 ml of methanol and 10 ml of benzene containing 13 g of 6-acetoxy-2-methyl-2-(4-nitrophenoxymethyl)-7-(1,1,3,3-tetramethylbutyl)chroman-4-one (prepared as described in Preparation 19), and the mixture was stirred for 30 minutes whilst ice-cooling. The reaction mixture was then poured into ice-water, neutralized with 10% w/v aqueous hydrochloric acid and extracted with benzene. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography, eluted with a 4:1 by volume mixture of benzene and ethyl acetate, to give the title compound.

Workup

  1. temperaturecooling
  2. extractionextracted with benzene
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with a 4:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-116aacd186ef4c1d8e3a6388875ac48c
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

Loading…