Sodium borohydride → (3-(2-((Triisopropylsilyl)oxy)ethyl)phenyl)methanol

HRID 41139Notes

Reaction equation

HRID 41139 reaction equation
[BH4-].[Na+].[CH:3]([Si:6]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[O:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14])([CH3:5])[CH3:4]>O1CCCC1.O>[CH:18]([Si:6]([CH:3]([CH3:5])[CH3:4])([CH:21]([CH3:23])[CH3:22])[O:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:13][OH:14])[CH:15]=[CH:16][CH:17]=1)([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 547576553-(2-((Triisopropylsilyl)oxy)ethyl)benzaldehyde

Product 1

HCID 54757656(3-(2-((Triisopropylsilyl)oxy)ethyl)phenyl)methanolYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.062 g, 1.63 mmol) was added to a mixture of 14 (0.500 g, 1.63 mmol) in tetrahydrofuran (4 mL) and water (0.25 mL). The reaction mixture was heated to reflux temperature for 2 h. After cooling, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue so obtained was dried under high vacuum to afford the desired compound as colorless oil. Yield: 99%.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature for 2 h
  3. temperatureAfter cooling
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue so obtained
  10. customwas dried under high vacuum

Sources & evidence

ORD record
ord-a870e9c963144b58968ae1ff49882552
Source dataset
uspto-grants-2013_09
Patent number
US08530520B2

Reaction notes

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