Water → 9-Methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carbaldehyde

HRID 1161429Notes

Reaction equation

HRID 1161429 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10]Br.[OH:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([O:22][CH3:23])[C:20]=1[OH:21])[CH:16]=[O:17].O>CN(C=O)C.C(OCC)(=O)C>[CH3:23][O:22][C:19]1[C:20]2[O:21][CH2:8][CH2:9][CH2:10][O:12][C:13]=2[CH:14]=[C:15]([CH:16]=[O:17])[CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 775353,4-Dihydroxy-5-methoxybenzaldehyde

Product 1

HCID 259171779-Methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carbaldehydeYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 1.5 g of potassium carbonate and 1.2 g of 1,3-dibromopropane to a solution of 920 mg of 3,4-dihydroxy-5-methoxybenzaldehyde [CAS No. 859785-71-0] in 10 ml of DMF, the mixture was stirred at 60° C. for 3 hours. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (604 mg) as an oil.

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationThe desiccating agent was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-cea6f6be94694f0abc9503f965a5ac0a
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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