Pyridine → HCID 22759221, compound

HRID 1704354Notes

Reaction equation

HRID 1704354 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8]/[CH:9]=[CH:10]/[CH:11]([OH:21])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].N1C=CC=CC=1>CCOCC>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8]/[CH:9]=[CH:10]/[CH:11]([O:21][C:22](=[O:24])[CH3:23])[CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 22759289HCID 22759289, compound

Product 1

HCID 22759221HCID 22759221, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(2-tetrahydropyranyloxy)-4-hydroxy-5-(4-fluorophenoxy)-trans-2-pentene (23.6 g., 0.08 mole), acetic anhydride (9.2 g., 0.09 mole), and pyridine (7.9 g., 0.1 mole) is heated at 55°-60° for 4 hours and then at 95° for an additional 4 hours. The solution is cooled, diluted with ether and washed with ice-cold saturated sodium carbonate solution, ice water (3 ×) and brine, and dried over sodium sulfate. Removal of solvent under vacuum leaves the title compound as a residual orange oil.

Workup

  1. temperatureis heated at 55°-60° for 4 hours
  2. temperatureThe solution is cooled
  3. washwashed with ice-cold saturated sodium carbonate solution, ice water (3 ×) and brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-eaed73e87a7c46f59cf0696b23e9c250
Source dataset
uspto-grants-1978_11
Patent number
US04126629

Reaction notes

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