Sodium borohydride → HCID 15694369, compound

HRID 1534375Notes

Reaction equation

HRID 1534375 reaction equation
[CH3:1][CH:2]([CH3:28])[CH2:3][C:4]([C:6]1[CH:25]=[CH:24][C:9]2[O:10][C:11]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[CH:17][C:12]=3[CH2:13][O:14][C:15](=[O:16])[C:8]=2[C:7]=1[O:26][CH3:27])=[O:5].[BH4-].[Na+]>O1CCCC1.O>[OH:5][CH:4]([C:6]1[CH:25]=[CH:24][C:9]2[O:10][C:11]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[CH:17][C:12]=3[CH2:13][O:14][C:15](=[O:16])[C:8]=2[C:7]=1[O:26][CH3:27])[CH2:3][CH:2]([CH3:28])[CH3:1]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 15703848HCID 15703848, compound

Product 1

HCID 15694369HCID 15694369, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

158 g (0.41 mmol) of 3-(3-methyl-1-butanonyl)-4,11-dimethoxy-9-methyl-7H-dibenzo[b,g][1,5]dioxocin-5-one are dissolved in 2 ml of tetrahydrofuran and 0.1 ml of water. 23 mg (0.61 mmol) of sodium borohydride are added to the solution and the mixture is stirred overnight at room temperature. Excess sodium borohydride is destroyed by addition of a few drops of acetic acid. The mixture is concentrated in vacuo, the residue is taken up in dichloromethane and the solution is washed with water. The organic phase is dried over magnesium sulphate, concentrated and purified by column chromatography on silica gel using petroleum ether/diethyl ether 1:1.

Workup

  1. customExcess sodium borohydride is destroyed by addition of a few drops of acetic acid
  2. concentrationThe mixture is concentrated in vacuo
  3. washthe solution is washed with water
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0e7e537f72c0439ba070309542d66de9
Source dataset
uspto-grants-1992_02
Patent number
US05089487

Reaction notes

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