o-Fluorobenzaldehyde → HCID 57456783, compound

HRID 559483Notes

Reaction equation

HRID 559483 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14][NH2:15])[CH3:11]>>[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14][N:15]=[CH:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[F:1])[CH3:11]

Participants

3

Reactant 2

HCID 67970o-FluorobenzaldehydeHCID 695242,2-Diethoxyethylamine

Product 1

HCID 57456783HCID 57456783, compound

Conditions

Temperature
100 °C

Procedure

2-Fluorobenzaldehyde (7.45 g), was added to aminoacetaldehyde diethylacetal (9.16 g) and the reaction heated to 100° C. for 3 h. After cooling, the mixture was transferred to a separating funnel and partitioned between diethyl ether and water. The ether layer was separated, dried over magnesium sulfate, filtered and concentrated under reduced pressure to leave an oil. Distillation at 0.6-0.8 mm collecting the fraction boiling at 102-106° C. afforded the title compound as a colourless oil.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was transferred to a separating funnel
  3. custompartitioned between diethyl ether and water
  4. customThe ether layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto leave an oil
  9. distillationDistillation at 0.6-0.8 mm
  10. customcollecting the fraction boiling at 102-106° C.

Sources & evidence

ORD record
ord-67f9c881a32d49b88fc7ab753872f04d
Source dataset
uspto-grants-2011_11
Patent number
US08063078B2

Reaction notes

Loading…