Реакция #429184

Уравнение реакции

methyl 3(R)-hydroxybutanoate

thiolacetic acid

PPh3

diethyl azodicarboxylate

→

title compound

Methyl 3(S)-(acetylthio)butanoate

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Другоеwas obtained
2. 2
   Температураto slowly warm to 25° C.
3. 3
   workup.STIRRINGwas stirred 16 h at 250° C
4. 4
   ДругоеMost THF was removed in vacuo and EtOAc (10 mL) and hexanes (100 mL)
5. 5
   workup.ADDITIONwere added
6. 6
   ДругоеInsolubles were removed by filtration
7. 7
   Другоеthe residue was purified by chromatography on silica gel

Методика

To a -23° C. solution of PPh3 (40 mmol, 10.48 g) in THF (100 mL) was added diethyl azodicarboxylate (40 mmol, 6.28 mL) dropwise and the mixture was stirred at -23° C. for 16 hours, during which time a white precipitate was obtained. A THF (30 mL) solution of methyl 3(R)-hydroxybutanoate (20 mm, 2.36 g) and thiolacetic acid (20 mmol, 2.85 mL) was slowly added and the mixture was allowed to slowly warm to 25° C. and was stirred 16 h at 250° C. Most THF was removed in vacuo and EtOAc (10 mL) and hexanes (100 mL) were added. Insolubles were removed by filtration and the residue was purified by chromatography on silica gel to afford the title compound. [α]D25 =-21° (c=3, CHCl3).

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