Hydrochloric Acid → HCID 19822180, compound

HRID 1030425Notes

Reaction equation

HRID 1030425 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[C:15]([CH3:18])([CH3:17])[CH3:16])[O:11][C:10]([CH3:30])([CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)[CH2:9][C:8]2=[O:31])(=O)C.[BH4-].[Na+].Cl>O1CCCC1.CO>[C:15]([C:14]1[CH:13]=[C:12]2[C:7]([CH:8]([OH:31])[CH2:9][C:10]([CH3:30])([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)[O:11]2)=[CH:6][C:5]=1[OH:4])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 13605827HCID 13605827, compound

Product 1

HCID 19822180HCID 19822180, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.0 g of 6-acetoxy-7-t-butyl-2-methyl-2-(4-nitrophenoxymethyl)chroman-4-one (prepared as described in Preparation 54) in 20 ml of tetrahydrofuran was dropped into a suspension containing 0.3 g of sodium borohydride in 10 ml of methanol whilst stirring over an ice bath. After the whole of the solution had been added, the reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was then ice-cooled again, acidified weakly with 10% w/v aqueous hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure to give crystals. Recrystallization of these crystals from a mixture of benzene and petroleum ether gave the title compound, melting at 194°-201° C.

Workup

  1. additionAfter the whole of the solution had been added
  2. stirringthe reaction mixture was stirred for 2 hours at room temperature
  3. temperatureice-cooled again
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed by evaporation under reduced pressure
  9. customto give crystals
  10. customRecrystallization of these crystals
  11. additionfrom a mixture of benzene and petroleum ether

Sources & evidence

ORD record
ord-2650b1dd87eb486c8e29de74ef67115a
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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