Sodium borohydride → (4-(3-(tert-Butyldimethylsilyloxy)propoxy)-2-methoxyphenyl)methanol

HRID 2207081Notes

Reaction equation

HRID 2207081 reaction equation
[BH4-].[Na+].[Si:3]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[C:17]([O:23][CH3:24])[CH:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>C1COCC1.CO.O.[Cl-].[Na+].O>[Si:3]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[C:17]([O:23][CH3:24])[CH:16]=1)([C:6]([CH3:8])([CH3:7])[CH3:9])([CH3:4])[CH3:5]

Participants

7

Reactant 2

HCID 4311764Sodium borohydrideHCID 879447074-(3-(tert-Butyldimethylsilyloxy)propoxy)-2-methoxybenzaldehyde

Product 1

HCID 68747805(4-(3-(tert-Butyldimethylsilyloxy)propoxy)-2-methoxyphenyl)methanolYield 86.3%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium borohydride (1.24 g) was added to a solution of the product from step (i) (21.3 g) in THF (100 mL), methanol (15 mL) and stirred at RT for 2.5 h. The mixture was diluted with water and brine, and extracted with EtOAc. And the combined organic solutions were dried and concentrated. The residue was purified by silica gel chromatography eluting with hexane/EtOAc to give the subtitle compound (18.5 g) as a colourless oil; 1H NMR: 7.14 (1H, d), 6.42-6.48 (2H, m), 4.61 (2H, d), 4.06 (2H, t), 3.84 (3H, s), 3.80 (2H, t), 2.15 (1H, t), 1.94-2.02 (2H, m), 0.89 (9H, s), 0.04 (6H, s).

Workup

  1. extractionextracted with EtOAc
  2. customAnd the combined organic solutions were dried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with hexane/EtOAc

Sources & evidence

ORD record
ord-80be83fa70074f5ea58f6db25901f294
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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