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

HRID 2269012Notes

Reaction equation

HRID 2269012 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-4dc7fbddf8bb4a46812db7e13885971f
Source dataset
uspto-grants-2001_12
Patent number
US06329387B2

Reaction notes

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