Penta-1,4-dien-3-ol → HCID 68278288, compound

HRID 530438Notes

Reaction equation

HRID 530438 reaction equation
[CH2:1]=[CH:2][CH:3]([OH:6])[CH:4]=[CH2:5].[F:7][CH2:8][CH:9]([NH2:12])[CH2:10][F:11].[N-]=C=O>ClCCCl.CO>[F:7][CH2:8][CH:9]([N:12]1[CH2:5][CH2:4][C:3](=[O:6])[CH2:2][CH2:1]1)[CH2:10][F:11]

Participants

6

Reactant 3

HCID 70204Penta-1,4-dien-3-olHCID 105034IsocyanateHCID 135916541,3-Difluoropropan-2-amine

Product 1

HCID 68278288HCID 68278288, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

1,4-Pentadien-3-ol (200 mg, 2.38 mmol) and IBX (999 mg, 3.57 mmol) were dissolved in DCE (15 mL) and heated at 70° C. for 3 h. The reaction mixture was filtered, diluted with MeOH (10 mL) and 2-fluoro-1-fluoromethyl-ethylamine (226 mg, 2.38 mmol) was added. The reaction mixture was stirred at 70° C. for 3 h. Isocyanate resin was added and the reaction mixture stirred at room temperature for 6 h, filtered and concentrated in vacuo to give the crude title compound (160 mg, 38%) as an orange gum. LCMS (ES+): 178.1 [MH]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionwas added
  3. stirringthe reaction mixture stirred at room temperature for 6 h
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fec31eafcbae4cdd89ae6b4f7526df3b
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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