Dimethylformamide → HCID 59810871, compound

HRID 2113708Notes

Reaction equation

HRID 2113708 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=1[OH:13].[CH3:15][N:16]([CH3:19])[CH:17]=O.[CH3:20]OC(OC)N(C)C>O>[F:1][CH:2]([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])/[CH:11]=[CH:15]/[N:16]([CH3:19])[CH3:17])=[CH:6][C:5]=1[O:13][CH3:20]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 53866232885132-72-9

Product 1

HCID 59810871HCID 59810871, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

Into a 1-necked flask were added 1-[4-(difluoromethoxy)-3-hydroxyphenyl]ethanone (0.317 g, 1.57 mmol), 16 mL of N,N-dimethylformamide, and N,N-dimethylformamide dimethy acetal (0.25 mL, 1.9 mmol). The mixture was heated to 140° C. overnight and after cooling to room temperature, poured into 50 mL water and extracted 3×50 mL ethyl acetate. The combined organic fractions were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient of 50% ethyl acetate in hexanes to 100% ethyl acetate over 30 minutes to give (2E)-1-[4-(difluoromethoxy)-3-methoxyphenyl]-3-(dimethylamino)prop-2-en-1-one (51 mg, 0.188 mmol) as a yellow oil.

Workup

  1. temperatureafter cooling to room temperature
  2. extractionextracted 3×50 mL ethyl acetate
  3. dry with materialThe combined organic fractions were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with a gradient of 50% ethyl acetate in hexanes to 100% ethyl acetate over 30 minutes

Sources & evidence

ORD record
ord-e6d75a53a5f0454c8ec735677192d839
Source dataset
uspto-grants-2008_10
Patent number
US07432266B2

Reaction notes

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