Water → (2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

HRID 1855227Notes

Reaction equation

HRID 1855227 reaction equation
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=[O:12])=[CH:10][C:4]=2[O:3]1.[BH4-].[Na+].O>C1COCC1>[F:13][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 27369732,2-Difluoro-5-formylbenzodioxoleHCID 4311764Sodium borohydride

Product 1

HCID 12814281(2,2-Difluoro-1,3-dioxaindan-5-yl)methanolYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,2-difluorobenzo[d][1,3]dioxole-5-carbaldehyde (125 g, 0.67 mol) in anhydrous THF (400 mL) was added NaBH4 (28 g, 0.74 mol) in portions at 0° C. The mixture was stirred for 1 h at 0° C., then poured into 500 mL of water. The mixture was extracted with ethyl acetate (200 mL×3). The organic phase was dried over Na2SO4 and concentrated in vacuo to give (2,2-difluorobenzo[d][1,3]dioxol-5-yl)methanol as colorless oil (120 g, 95%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (200 mL×3)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c60d36b19ad4e36aaabdee5560d7ecb
Source dataset
uspto-grants-2015_02
Patent number
US08962856B2

Reaction notes

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