Chloroform → {3-[(Tert-butyldimethylsilyl)oxy]-4-methoxyphenyl}methanol

HRID 1028923Notes

Reaction equation

HRID 1028923 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].C(Cl)(Cl)Cl>CO>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 3595583-((tert-Butyldimethylsilyl)oxy)-4-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 11572549{3-[(Tert-butyldimethylsilyl)oxy]-4-methoxyphenyl}methanolYield 73.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cooled solution of 3-[(tert-Butyldimethylsilyl)oxy]-4-methoxybenzaldehyde 13 (17.5 g, 65.7 mmol) in methanol (100 mL) under nitrogen, sodium borohydride (2.98 g, 78.8 mmol) was added and stirred at room temperature for 30 min. After the reaction was complete as indicated by TLC (chloroform on silica gel plate), ice was added to the reaction mixture and extracted with ethyl acetate. The organic layer was separated, washed with water and dried. Removal of solvent in vacuo yielded on yellow oil 14 (73.5%). 1H NMR: δ 0.18 (s, 6H, 2×CH3), 1.00 (s, 9H, 3×CH3), 1.90 (br s, 1H, OH), 3.82 (s, 3H, OCH3), 4.56 (s, 2H, CH2OH), 6.94 (br s, 3H, Ar—H). Anal. Calcd for C14H24O3Si: C, 62.64, H, 9.01. Found: C, 62.59, H, 9.03.

Workup

  1. additionwas added to the reaction mixture
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-733c8dd9dd1245078779f65fc303d88b
Source dataset
uspto-grants-2014_05
Patent number
US08735620B2

Reaction notes

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