Water → Methyl 3-(benzylthio)-2-methoxypropanoate

HRID 1590100Notes

Reaction equation

HRID 1590100 reaction equation
[C:1]([S:4][CH2:5][CH:6](CC)[C:7]([O:9][CH2:10]C)=[O:8])(=O)[CH3:2].[CH2:14](S)[C:15]1C=C[CH:18]=[CH:17][CH:16]=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O.C1C[O:44][CH2:43]C1>>[CH2:1]([S:4][CH2:5][CH:6]([O:44][CH3:43])[C:7]([O:9][CH3:10])=[O:8])[C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 5

HCID 962WaterHCID 7509Benzyl mercaptanHCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 15025921Ethyl 2-(acetylthiomethyl)butanoate

Product 1

HCID 19769446Methyl 3-(benzylthio)-2-methoxypropanoate

Procedure

To a solution of the propenoate of Step 1 (26.93 g, 0.23 mmol) in THF (20 mL) at 0° C. was added benzyl mercaptan (23.0 mL, 0.23 mol) followed by 1M THF solution of Bu4NF (20 mL). The mixture was stirred at room temperature for 1 hour. The reaction was poured into H2O and extracted with EtOAc, washed with brine, dried and concentrated to yield the title compound. Although the material is essentially pure it can be distilled under vacuum, b.p. 115°-130° C./1 mmHg.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-06379cadbab8415aa29a9a0cca0ec938
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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