Trifluoroacetic acid → HCID 20251751, compound

HRID 1284467Notes

Reaction equation

HRID 1284467 reaction equation
C1(/[C:7](/[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])C=CC=CC=1.[O-:21][C:22]#[N:23].[Na+].FC(F)(F)C(O)=O>C(Cl)Cl>[C:22]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]/[CH:8]=[CH:7]/[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)(=[O:21])[NH2:23]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 517096Sodium CyanateHCID 13417327HCID 13417327, compound

Product 1

HCID 20251751HCID 20251751, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-7-Phenyl-7-(3-pyridyl)-6-hepten-1-ol (2.0 g, 7.4 mmoles) was dissolved in methylene chloride (20 ml), and sodium cyanate (0.50 g, 7.7 mmoles) and trifluoroacetic acid (5 ml) were added. The mixture was stirred at room temperature for 20 hours and concentrated under reduced pressure. The residue was shaken with potassium carbonate (1 g), water (20 ml) and methylene chloride (50 ml), and the organic layer was separated, washed with water, dried and concentrated. Recrystallization of the residue from isopropyl ether gave 1-carbamoyloxy-(E)-7-(3-pyridyl)-6-heptene (1.82 g, 79%) (Compound Id-23).

Workup

  1. concentrationconcentrated under reduced pressure
  2. stirringThe residue was shaken with potassium carbonate (1 g), water (20 ml) and methylene chloride (50 ml)
  3. customthe organic layer was separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. customRecrystallization of the residue from isopropyl ether

Sources & evidence

ORD record
ord-e96b5c272bd1468a9598e531fd04837b
Source dataset
uspto-grants-1986_01
Patent number
US04563446

Reaction notes

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