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Diethyl Ether → Methyl 3-((3-methoxy-3-oxopropyl)thio)-3-methylbutanoate

HRID 656037
Notes
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Reaction equation

HRID 656037 reaction equation
[CH3:1][C:2]([CH3:8])=[CH:3][C:4]([O:6][CH3:7])=[O:5].N1CCCCC1.[SH:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].CCOCC>CO>[CH3:7][O:6][C:4](=[O:5])[CH2:3][C:2]([S:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])([CH3:8])[CH3:1]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8082PiperidineHCID 13546Methyl 3-methyl-2-butenoateHCID 18050Methyl 3-mercaptopropionate

Product 1

HCID 59332631Methyl 3-((3-methoxy-3-oxopropyl)thio)-3-methylbutanoateYield 97.23%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Conditions

Temperature
60 °C

Procedure

To a well-stirred mixture of methyl 3-methylbut-2-enoate (50.0 g, 438 mmol), 40% Triton B in MeOH (5 mL) and piperidine (4 mL) were added dropwise at 0° C., then methyl 3-mercaptopropanoate (50 g, 396 mmol) was added. After stirring for 24 h at 60° C., Et2O (500 mL) was added, and the organic phase washed thoroughly with 10% H2SO4 (150 mL), sat. NaHCO3 (150 mL), and brine (200 mL) successively, dried over Na2SO4 and evaporated under vacuum to give the title compound as a colorless oil (90.1 g, 97.23%).

Workup

  1. washthe organic phase washed thoroughly with 10% H2SO4 (150 mL), sat. NaHCO3 (150 mL), and brine (200 mL) successively
  2. dry with materialdried over Na2SO4
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-338d8ceb72b945ea87ade113353cdace
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071584B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes