Methyl vinyl ketone → Methyl 3-[(3-oxobutyl)thio]propanoate

HRID 907459Notes

Reaction equation

HRID 907459 reaction equation
[CH:1]([C:3]([CH3:5])=[O:4])=[CH2:2].[SH:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].C(N(CC)CC)C>C1COCC1>[O:4]=[C:3]([CH3:5])[CH2:1][CH2:2][S:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 8471TriethylamineHCID 18050Methyl 3-mercaptopropionate

Product 1

HCID 11344502Methyl 3-[(3-oxobutyl)thio]propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl vinyl ketone (90%, 185 ml, 2.0 mol) was added portionwise to a solution of methyl 3-mercaptopropionate (200 ml, 1.83 mol) and triethylamine (26 ml, 0.1 equiv) in THF (2.4 L). This mixture was heated slowly to 50 C and stirred at that temperature for 4.5 h. The solvent was then evaporated to afford 11 as an oil.

Workup

  1. temperatureThis mixture was heated slowly to 50 C
  2. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-c1af50cae2dc449fb75bfad87ada9019
Source dataset
uspto-grants-2011_09
Patent number
US08013159B2

Reaction notes

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