Dimethylformamide → HCID 117992086, compound

HRID 531016Notes

Reaction equation

HRID 531016 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.CN(C=O)C.[CH:11]1([C:14]2[CH:15]=[C:16]([CH:19]=[C:20]([O:23][CH2:24][CH3:25])[C:21]=2[OH:22])[CH:17]=[O:18])[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>O>[CH:11]1([C:14]2[CH:15]=[C:16]([CH:19]=[C:20]([O:23][CH2:24][CH3:25])[C:21]=2[O:22][CH2:2][CH:3]2[CH2:5][CH2:4]2)[CH:17]=[O:18])[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 90423706HCID 90423706, compound

Product 1

HCID 117992086HCID 117992086, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

(Bromomethyl)cyclopropane (0.781 mL) was added to a DMF (10 mL) suspension of 3-cyclopropyl-5-ethoxy-4-hydroxybenzaldehyde (830 mg) and potassium carbonate (1.11 g), and the mixture was stirred at 70° C. for 5 hours. The reaction mixture was allowed to cool to room temperature, and then, water was added thereto, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (1.03 g).

Workup

  1. temperatureto cool to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe obtained organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bb494eefdbfb48dc82593015456f33da
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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