2-Mercaptoethanol → HCID 21242306, compound

HRID 1761777Notes

Reaction equation

HRID 1761777 reaction equation
[CH3:1]/[C:2](/[CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:18])/[CH2:11][CH2:12][C:13](=[O:17])[C:14]([CH3:16])=[CH2:15])=[CH:3]\[C:4]([NH2:6])=[O:5].S[CH2:20][CH2:21][OH:22].C(N(CC)CC)C>CO>[OH:22][CH2:21][CH2:20][CH2:15][CH:14]([CH3:16])[C:13](=[O:17])[CH2:12][CH2:11]/[C:10](/[CH3:18])=[CH:9]/[CH2:8][CH2:7]/[C:2](/[CH3:1])=[CH:3]/[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 21242302HCID 21242302, compound

Product 1

HCID 21242306HCID 21242306, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.1 g (0.016 mol) of (E,E)-3,7,11-trimethyl-10-oxo-2,6,11-dodecatrienamide in 125 ml of methanol is treated with 3.5 ml of 2-mercaptoethanol and 7 ml of triethylamine. The solution is stirred at room temperature for 18 hours. 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-methanol 10:1. There is obtained (2E,6E)-12-(2-hydroxyethyl)-3,7,11-trimethyl-10-oxo-2,6-dodecadienamide which exhibits the following absorption bands in the IR spectrum: 3340 cm-1, 3201 cm-1, 2924 cm-1, 1707 cm-1, 1669 cm-1, 1608 cm-1, 1409 cm-1, 1369 cm-1, 1305 cm-1, 1046 cm-1, 1012 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-methanol 10:1

Sources & evidence

ORD record
ord-79c24cc4698843b781618bb68a43e17b
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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