Sodium borohydride → (5-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorophenyl)methanol

HRID 446358Notes

Reaction equation

HRID 446358 reaction equation
[BH4-].[Na+].[Si:3]([O:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([F:21])=[C:17]([CH:20]=1)[CH:18]=[O:19])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>C(O)C>[Si:3]([O:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([F:21])=[C:17]([CH2:18][OH:19])[CH:20]=1)([C:6]([CH3:8])([CH3:9])[CH3:7])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 579890665-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde2×

Product 1

HCID 58168522(5-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorophenyl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (1.33 g) was added portionwise over 30 minutes to a solution at 0° C. of 5-(2-(tert-butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde [Aromatic Intermediate 3, step b] (9.9 g) in ethanol (120 mL). The reaction mixture was then stirred at room temperature for 30 minutes before being reduced to half the initial volume by concentration under reduced pressure. The residue was partitioned between ethyl acetate and brine, the organic layer was washed with brine, dried, filtered and the solvent concentrated under reduced pressure. The crude product was purified by flash silica chromatography using 12% ethyl acetate in isohexane as solvent. Fractions containing the product were concentrated to dryness to afford the titled compound. Yield 7.30 g.

Workup

  1. concentrationby concentration under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and brine
  3. washthe organic layer was washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationthe solvent concentrated under reduced pressure
  7. customThe crude product was purified by flash silica chromatography
  8. additionFractions containing the product
  9. concentrationwere concentrated to dryness

Sources & evidence

ORD record
ord-84a7fc188ad84a59ad7615f1df23d56d
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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