Water → 2-(2,3-Dihydro-1,4-benzodioxin-6-yl)ethan-1-ol

HRID 1053787Notes

Reaction equation

HRID 1053787 reaction equation
B.C1COCC1.[O:7]1[CH2:12][CH2:11][O:10][C:9]2[CH:13]=[C:14]([CH2:17][C:18](O)=[O:19])[CH:15]=[CH:16][C:8]1=2.O>C1COCC1>[O:7]1[CH2:12][CH2:11][O:10][C:9]2[CH:13]=[C:14]([CH2:17][CH2:18][OH:19])[CH:15]=[CH:16][C:8]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 870201,4-Benzodioxan-6-ylacetic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 197468082-(2,3-Dihydro-1,4-benzodioxin-6-yl)ethan-1-olYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BH3.THF (44 mL, 44 mmol, 1 M/THF) was added to a 0° C. solution of 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acetic acid (3.419 g, 17.6 mmol) in THF (8.8 mL). The reaction was allowed to warm to room temperature and after 2 h, 20 mL H2O was added slowly by syringe. The resulting mixture was extracted with ethyl acetate, the organic portion was washed with brine, and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (3.059 g, 99%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washthe organic portion was washed with brine
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cc51561050704db3ba33c61cfc045b75
Source dataset
uspto-grants-2016_07
Patent number
US09394273B2

Reaction notes

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