Sodium Bicarbonate → (4-(Tert-butyldimethylsilyloxy)-3-ethoxyphenyl)methanol

HRID 718540Notes

Reaction equation

HRID 718540 reaction equation
[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH2:18][CH3:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].C([O-])(O)=O.[Na+]>CCO>[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[O:17][CH2:18][CH3:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 858559344-[(Tert-butyldimethylsilyl)oxy]-3-ethoxybenzaldehyde

Product 1

HCID 67984855(4-(Tert-butyldimethylsilyloxy)-3-ethoxyphenyl)methanolYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(tert-butyldimethylsilyloxy)-3-ethoxybenzaldehyde (12.7 g, 45.4 mmol, 1.0 equiv.) in EtOH (50 mL), NaBH4 (868 mg, 22.7 mmol, 0.5 equiv.) was added at 0° C., and the mixture was stirred at 0° C. for 2 h. After slow addition of sat. aq. NaHCO3-solution, the aqueous layer was extracted with EtOAc (2×). The combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated to yield 12.6 g (98%) of (4-(tert-butyldimethylsilyloxy)-3-ethoxyphenyl)methanol as a light yellow oil.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (2×)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d19d3ad1cf7c41cb9b4a2922dd6a934b
Source dataset
uspto-grants-2015_11
Patent number
US09193935B2

Reaction notes

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