3-Methyl-2-butanone → HCID 66726288, compound

HRID 1024493

Reaction equation

HRID 1024493 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]=O)=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1.[CH3:14][CH:15]([CH3:19])[C:16](=[O:18])[CH3:17].[OH-].[Na+]>CO>[O:1]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]=[CH:17][C:16](=[O:18])[CH:15]([CH3:19])[CH3:14])=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 112513-Methyl-2-butanoneHCID 14798Sodium HydroxideHCID 27763883,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde

Product 1

HCID 66726288HCID 66726288, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The MeOH (5 mL) solution of 3,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde (445 mg) and 3-methyl-2-butanone (195 mg) was treated with aq. sodium hydroxide (1N, 1 ml) and the mixture was stirred for 24 hours. The reaction was partitioned between 10 ml water and 40 ml ethyl acetate. The organic layer was then sequentially washed with aq. hydrochloric acid (1N, 20 ml), water (20 ml), and Brine (20 ml) and then concentrated under reduced pressure. The residue was purified with flash chromatography on silica (33% ethyl acetate in hexane) to give the desired product as a white crystal.

Workup

  1. customThe reaction was partitioned between 10 ml water and 40 ml ethyl acetate
  2. washThe organic layer was then sequentially washed with aq. hydrochloric acid (1N, 20 ml), water (20 ml), and Brine (20 ml)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with flash chromatography on silica (33% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-92691c7ded8f4b29ac0610f63ab42051
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Linked notes

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