3-(Benzodioxol-5-yl)propionic acid → 1,3-Benzodioxole-5-propanol

HRID 1265038Notes

Reaction equation

HRID 1265038 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][C:12](O)=[O:13])=[CH:4][C:3]=2[O:2]1.B.O1CCCC1>CCOCC>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 648103-(Benzodioxol-5-yl)propionic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 110304141,3-Benzodioxole-5-propanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-(3,4-methylenedioxyphenyl)propionic acid (1.0 g, 5.2 mmoles) in ether (100 ml) at 0° C. was added borane-tetrahydrofuran (1.0 M, 6.2 ml, 6.2 mmoles). The cooling bath was removed and 15 minutes later methanol (5 ml) was slowly added. One hour later the reaction was washed with H2O (200 ml), and then the organic layer was dried (MgSO4), filtered and concentrated to collect 0.91 g (98%) of the title compound as a colorless oil.

Workup

  1. customThe cooling bath was removed and 15 minutes later methanol (5 ml)
  2. additionwas slowly added
  3. washOne hour later the reaction was washed with H2O (200 ml)
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto collect 0.91 g (98%) of the title compound as a colorless oil

Sources & evidence

ORD record
ord-6fa76b106bab47b3b487deb693a4d906
Source dataset
uspto-grants-2003_04
Patent number
US06545014B2

Reaction notes

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