Water → (S)-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1,2-butanediol

HRID 2295462Notes

Reaction equation

HRID 2295462 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15][C@@:16]([OH:20])([CH3:19])[CH:17]=[O:18].[BH4-].[Na+].O>C(O)C>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15][C@:16]([CH3:19])([OH:20])[CH2:17][OH:18]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 13100531HCID 13100531, compound

Product 1

HCID 11129761(S)-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1,2-butanediolYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

180 mg (0.643 mmole) of (S)-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-hydroxy-2-methylbutanal was dissolved in 5 ml of ethanol, and 30 mg (0.79 mmole) of sodium borohydride was added, followed by stirring at room temperature for 30 minutes. Water was added to the reaction solution which was then extracted with methylene chloride. The organic extract was washed with a saturated aqueous solution of sodium chloride dried over sodium sulfate and freed from the solvent under reduced pressure. The residue was purified on silica gel column to obtain 156 mg (86%) of (S)-4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1,2-butanediol.

Workup

  1. extractionwas then extracted with methylene chloride
  2. extractionThe organic extract
  3. washwas washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-f3d371da0622476eb6e0a6d2ba17ca28
Source dataset
uspto-grants-1984_01
Patent number
US04424389

Reaction notes

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