Sodium borohydride → (4-[1,3]Dioxolan-2-yl-3-fluoro-phenyl)-methanol

HRID 1691335

Reaction equation

HRID 1691335 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[F:14].[BH4-].[Na+]>CO>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][C:7]=1[F:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 592554594-[1,3]Dioxolan-2-yl-3-fluoro-benzaldehyde

Product 1

HCID 59255152(4-[1,3]Dioxolan-2-yl-3-fluoro-phenyl)-methanolYield 24.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol solution (200 mL) of 4-[1,3]dioxolan-2-yl-3-fluoro-benzaldehyde (10 g, 50.9 mmol) described in Manufacturing Example 204-1-2 was added sodium borohydride (2.12 g, 56 mmol), which was stirred for 1 hour at room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1) to obtain the title compound (2.44 g, 24%).

Workup

  1. customThis mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1)

Sources & evidence

ORD record
ord-f111a858a75742d085a908b27fffc5e1
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Linked notes

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