Water → HCID 69363687, compound

HRID 49285Notes

Reaction equation

HRID 49285 reaction equation
[BH4-].[Na+].[O:3]([C:21]1[CH:28]=[C:27]([O:29][CH3:30])[C:24]([CH:25]=[O:26])=[C:23]([O:31][CH3:32])[CH:22]=1)[Si:4]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>O1CCCC1>[O:3]([C:21]1[CH:22]=[C:23]([O:31][CH3:32])[C:24]([CH2:25][OH:26])=[C:27]([O:29][CH3:30])[CH:28]=1)[Si:4]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 877994184-t-Butyldiphenylsiloxy-2,6-dimethoxybenzaldehyde

Product 1

HCID 69363687HCID 69363687, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (519.0 mg, 13.73 mmol) was added to an ice-cold solution of 4-t-butyldiphenylsiloxy-2,6-dimethoxybenzaldehyde (3.85 g, 9.15 mmol) in tetrahydrofuran (40 mL), and the mixture was stirred at room temperature for 2 hours and 30 minutes. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford crude 4-t-butyldiphenylsiloxy-2,6-dimethoxybenzyl alcohol as a colorless crystalline powder (melting point: 127.5-129.0° C.) (4.01 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26c54461e21b4a2492f22c280ad4dba5
Source dataset
uspto-grants-2004_03
Patent number
US06706703B2

Reaction notes

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