2-Mercaptoethanol → HCID 86735636, compound

HRID 261398Notes

Reaction equation

HRID 261398 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[C:11]1[C:12](=[O:18])[CH2:13][CH:14](OC)[CH:15]=1)([O:3][CH3:4])=[O:2].[SH:19][CH2:20][CH2:21][OH:22].C[O-].[Na+]>CO>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[C:11]1[C:12](=[O:18])[CH2:13][CH:14]([S:19][CH2:20][CH2:21][OH:22])[CH:15]=1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 10942334Sodium MethoxideHCID 86735637HCID 86735637, compound

Product 1

HCID 86735636HCID 86735636, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 7.57 g (30 mmols) of 2-(6-carbomethoxy-2-cis-hexenyl)-4-methoxycyclopent-2-en-1-one (Example 283) and 2.46 g (31.5 mmols) of β-mercaptoethanol in 150 ml of methanol is added 15 ml of N/10 sodium methoxide in methanol solution. After 50 minutes at room temperature the solution is acidified with 0.27 ml of gl. acetic acid and partitioned with ether-brine. The ether extract is washed with brine, dried over magnesium sulfate, and concentrated. The residue is subjected to column chromatography on silica-gel to provide an oil.

Workup

  1. customacetic acid and partitioned with ether-brine
  2. extractionThe ether extract
  3. washis washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto provide an oil

Sources & evidence

ORD record
ord-fc04cccbaa544a4e85db73be1f88328e
Source dataset
uspto-grants-1979_08
Patent number
US04165331

Reaction notes

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