Sodium borohydride → (7-Fluoro-benzo[1,3]dioxol-5-yl)-methanol

HRID 503275Notes

Reaction equation

HRID 503275 reaction equation
[F:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH:11]=[O:12])[CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH2:11][OH:12])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 591291537-Fluorobenzo[d][1,3]dioxole-5-carbaldehyde

Product 1

HCID 59129331(7-Fluoro-benzo[1,3]dioxol-5-yl)-methanolYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-fluoro-benzo[1,3]dioxole-5-carbaldehyde (0.80 g, 4.7 mmol) in MeOH (50 mL) was added NaBH4 (0.36 g, 9.4 mmol) in portions at 0° C. The mixture was stirred at this temperature for 30 min and was then concentrated to dryness. The residue was dissolved in EtOAc. The EtOAc layer washed with water, dried over Na2SO4 and concentrated to dryness to afford (7-fluoro-benzo[1,3]dioxol-5-yl)-methanol (0.80 g, 98%), which was directly used in the next step.

Workup

  1. concentrationwas then concentrated to dryness
  2. dissolutionThe residue was dissolved in EtOAc
  3. washThe EtOAc layer washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-450c530f3195474991efe0a1a6895090
Source dataset
uspto-grants-2010_08
Patent number
US07776905B2

Reaction notes

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