Pyridine → HCID 86742988, compound

HRID 1761760Notes

Reaction equation

HRID 1761760 reaction equation
[OH:1][CH2:2]/[CH:3]=[C:4](\[CH3:17])/[CH2:5][CH2:6]/[CH:7]=[C:8](/[CH3:16])\[CH2:9][CH2:10][C:11](=[O:15])[C:12]([CH3:14])=[CH2:13].N1C=CC=CC=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>C(Cl)Cl>[C:24]([O:1][CH2:2]/[CH:3]=[C:4](\[CH3:17])/[CH2:5][CH2:6]/[CH:7]=[C:8](/[CH3:16])\[CH2:9][CH2:10][C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86742987HCID 86742987, compound

Product 1

HCID 86742988HCID 86742988, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.5 g (0.0021 mol) of (6Z,10E)-12-hydroxy-2,6,10-trimethyl-1,6,10-dodecatrien-3-one dissolved in 5 ml of methylene chloride and 1.3 ml of pyridine is treated with 1 ml of acetic anhydride. The solution is stirred at room temperature for 18 hours under argon. After removing the solvent the residue is taken up three times in toluene and freed from solvent on a rotary evaporator. The residue is chromatographed on silica gel with ether-hexane 1:5. There is obtained (2E,6Z)-3,7,11-trimethyl-10-oxo-2,6,11-dodecatrienyl acetate which has the following bands in the IR spectrum: 1739 cm-1, 1675 cm-1, 1629 cm-1, 1449 cm-1, 1370 cm-1, 948 cm-1.

Workup

  1. customAfter removing the solvent the residue
  2. customfreed from solvent on a rotary evaporator
  3. customThe residue is chromatographed on silica gel with ether-hexane 1:5

Sources & evidence

ORD record
ord-a718ce6f11294e55ae3948926d593e61
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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