2-Mercaptoethanol → HCID 86742996, compound

HRID 1761770Notes

Reaction equation

HRID 1761770 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].[SH:18][CH2:19][CH2:20][OH:21].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:18][CH2:19][CH2:20][OH:21]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 86742985HCID 86742985, compound

Product 1

HCID 86742996HCID 86742996, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 300 mg (0.0013 mol) of (6E,10Z)-12-hydroxy-2,6,10-trimethyl-1,6,10-dodecatrien-3-one in 10 ml of methanol is treated with 0.27 ml of 2-mercapto-ethanol and 0.53 ml of triethylamine. The solution is stirred at room temperature for 18 hours under argon. After removing the solvent on a rotary evaporator the residue is treated with water and methylene chloride. After extraction the organic phase is dried and freed from solvent on a rotary evaporator. The residue is chromatographed on silica gel with ether-methanol 50:1. There is obtained (6E,10Z)-12-hydroxy-1-[(2-hydroxyethyl)thio]-2,6,10-trimethyl-6,10-dodecadien-3-one which has the following absorption bands in the IR spectrum: 3369 cm-1, 1708 cm-1, 1667 cm-1, 1450 cm-1, 1044 cm-1, 1055 cm-1.

Workup

  1. customAfter removing the solvent
  2. customon a rotary evaporator the residue
  3. additionis treated with water and methylene chloride
  4. extractionAfter extraction the organic phase
  5. customis dried
  6. customfreed from solvent on a rotary evaporator
  7. customThe residue is chromatographed on silica gel with ether-methanol 50:1

Sources & evidence

ORD record
ord-d4da6e0fe5734f6bb4dd0236d1bc3876
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

Loading…