Sodium borohydride → 1,3-Benzodioxole-5-methanol, 6-fluoro-

HRID 1991610Notes

Reaction equation

HRID 1991610 reaction equation
[F:1][C:2]1[C:3]([CH:11]=[O:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[BH4-].[Na+]>CO.CCOC(C)=O>[F:1][C:2]1[C:3]([CH2:11][OH:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 143844436-Fluoro-1,3-dioxaindane-5-carbaldehyde

Product 1

HCID 591291851,3-Benzodioxole-5-methanol, 6-fluoro-Yield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 6-fluoro-benzo[1,3]dioxole-5-carbaldehyde (700 mg, 4.2 mmol) in MeOH (50 mL) was added NaBH4 (320 mg, 8.4 mmol) in portions at 0° C. The mixture was stirred at this temperature for 30 min and was then concentrated in vacuo to give a residue. The residue was dissolved in EtOAc and the organic layer was washed with water, dried over Na2SO4, and concentrated in vacuo to afford (6-fluoro-benzo[1,3]dioxol-5-yl)-methanol (650 mg, 92%), which was directly used in the next step.

Workup

  1. concentrationwas then concentrated in vacuo
  2. customto give a residue
  3. washthe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b43b1e11a0b6422e97ff586c1c48ef64
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

Loading…