Pyridine → HCID 86742998, compound

HRID 1761772Notes

Reaction equation

HRID 1761772 reaction equation
[OH:1][CH2:2]/[CH:3]=[C:4](/[CH3:23])\[CH2:5][CH2:6]/[CH:7]=[C:8](\[CH3:22])/[CH2:9][CH2:10][C:11](=[O:21])[CH:12]([CH3:20])[CH2:13][S:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].N1C=CC=CC=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>C(Cl)Cl>[C:30]([O:1][CH2:2]/[CH:3]=[C:4](/[CH3:23])\[CH2:5][CH2:6]/[CH:7]=[C:8](\[CH3:22])/[CH2:9][CH2:10][C:11](=[O:21])[CH:12]([CH3:20])[CH2:13][S:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86742997HCID 86742997, compound

Product 1

HCID 86742998HCID 86742998, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 300 mg (0.00088 mol) of methyl [[(6E, 10Z)-12-hydroxy-2,6,10-trimethyl-3-oxo-6,10-dodecadienyl]thio]acetate in 5 ml of methylene chloride is treated with 0.5 ml of pyridine and 0.4 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. There is obtained (2Z,6E)-12-[[(methoxycarbonyl)methyl]thio]-3,7,11-trimethyl-10-oxo-2,6-dodecadienyl acetate which exhibits the following bands in the IR spectrum: 1710 cm-1, 1657 cm-1, 1552 cm-1, 1445 cm-1, 1375 cm-1, 1290 cm-1, 1235 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

Sources & evidence

ORD record
ord-1383ff6f97684a92ab8437ce2e945f52
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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