Triethylamine → HCID 86742997, compound

HRID 1761771Notes

Reaction equation

HRID 1761771 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].[C:18]([O:22][CH3:23])(=[O:21])[CH2:19][SH:20].C(N(CC)CC)C>CO>[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])[CH:12]([CH3:14])[CH2:13][S:20][CH2:19][C:18]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 86742985HCID 86742985, compound

Product 1

HCID 86742997HCID 86742997, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4 g (0.0017 mol) of (6E,10Z)-12-hydroxy-2,6,10-trimethyl-1,6,10-dodecatrien-3-one in 13 ml of methanol is treated with 4.7 ml of methyl thioglycolate and 7.1 ml of triethylamine. The solution is stirred at room temperature for 18 hours under argon. After removing the solvent the residue is worked-up with water and methylene chloride. The organic phase is dried and freed from solvent. The residue is chromatographed on silica gel with ether. There is obtained methyl [[(6E,10Z)-12-hydroxy-2,6,10-trimethyl-3-oxo-6,10-dodecadienyl]thio]acetate which has the following bands in the IR spectrum: 1736 cm-1, 1711 cm-1, 1437 cm-1, 1408 cm-1, 1281 cm-1, 1137 cm-1, 1007 cm-1.

Workup

  1. customAfter removing the solvent the residue
  2. customThe organic phase is dried
  3. customThe residue is chromatographed on silica gel with ether

Sources & evidence

ORD record
ord-f34b58e2b3404d59bd5461c72ed7371a
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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