Pyridine → HCID 86742986, compound

HRID 1761754Notes

Reaction equation

HRID 1761754 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 86742985HCID 86742985, compound

Product 1

HCID 86742986HCID 86742986, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.5 g (0.0021 mol) of (6E,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 the solvent on a rotary evaporator. The residue is chromatographed on silica gel with ether-hexane 1:5. There is obtained (2Z,6E)-3,7,11-trimethyl-10-oxo-2,6,11-dodecatrienyl acetate which has the following bands in the IR spectrum: 1735 cm-1, 1677 cm-1, 1630 cm-1, 1448 cm-1, 1368 cm-1, 950 cm-1.

Workup

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

Sources & evidence

ORD record
ord-28b5c8f07fc34bda9699c6cc492a5bca
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

Loading…