Dimethylformamide → HCID 86658677, compound

HRID 42684Notes

Reaction equation

HRID 42684 reaction equation
O[C:2]1[CH:10]=[CH:9][C:5]2O[CH2:7][O:8][C:4]=2[C:3]=1[CH:11]=[O:12].[C:13]([O-:16])([O-])=[O:14].[K+].[K+].[CH3:19]N(C)C=O>>[CH2:7]([O:8][C:4]1[CH:5]=[CH:9][C:10]2[O:14][CH2:13][O:16][C:2]=2[C:3]=1[CH:11]=[O:12])[CH3:19]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 183159245-Hydroxy-1,3-benzodioxole-4-carbaldehyde

Product 1

HCID 86658677HCID 86658677, compound

Procedure

Under argon to a stirred solution of 5-hydroxy-1,3-benzodioxole-4-carbaldehyde (0.151 g, 0.91 mmol) and K2CO3 (1 eq) in dry N,N-dimethylformamide (2 ml) ethyl-bromide (1 eq) was added. The mixture was stirred at room temperature for 18 h until the starting material had been consumed (monitored by TLC). Then the mixture was poured onto ice water (15 ml). This aqueous phase was extracted with ethyl acetate (1×40 ml, then 2×15 ml) and the combined organic phases were washed with water and dried over anhydrous MgSO4. The solvent was evaporated in vacuo, and the crude product was purified by column chromatography with a mixture of n-hexane:ethyl acetate (4:1) as the eluent.

Workup

  1. customhad been consumed (monitored by TLC)
  2. additionThen the mixture was poured onto ice water (15 ml)
  3. extractionThis aqueous phase was extracted with ethyl acetate (1×40 ml
  4. wash2×15 ml) and the combined organic phases were washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. customThe solvent was evaporated in vacuo
  7. customthe crude product was purified by column chromatography with a mixture of n-hexane:ethyl acetate (4:1) as the eluent

Sources & evidence

ORD record
ord-31914fd280094c9e86577ce79167868a
Source dataset
uspto-grants-2013_09
Patent number
US08536210B2

Reaction notes

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