Pyridine → HCID 86742991, compound

HRID 1761766Notes

Reaction equation

HRID 1761766 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 86742990HCID 86742990, compound

Product 1

HCID 86742991HCID 86742991, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.5 g (0.0021 mol) of (6Z,10Z)-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 each time on a rotary evaporator. The residue is chromatographed on silica gel with ether-hexane 1:5. There is obtained (2Z,6Z)-3,7,11-trimethyl-10-oxo-2,6,11-dodecatrienyl acetate which has the following bands in the IR spectrum: 1742 cm-1, 1671 cm-1, 1634 cm-1, 1442 cm-1, 1367 cm-1, 951 cm-1.

Workup

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

Sources & evidence

ORD record
ord-7d849f959c65420ca5b347f892282ab0
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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