Реакция #51792

Уравнение реакции

tetrabutylammoniumflouride

4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one

toluene-4-thiosulfonic acid S-[5-(tert-butyl-dimethyl-silanyloxymethyl)-2-isopropyl-thiophen-3-yl]ester

NEt3

→

title compound

4-Hydroxy-3-(5-hydroxymethyl-2-isopropyl-thiophen-3-ylsulfanyl)-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one

Растворители

THF

acetonitrile

H2O

Условия реакции

Обработка

1. 1
   ДругоеThe title compound was prepared
2. 2
   ДругоеAs part of the purification
3. 3
   workup.DISSOLUTIONby dissolving the crude
4. 4
   Экстракцияextracted with EtOAc
5. 5
   Сушкаdried (MgSO4)
6. 6
   Концентрированиеconcentrated
7. 7
   ПромывкаThe resulting residue was then submitted to column chromatography (eluting with 3% MeOH in CH2Cl2)

Методика

The title compound was prepared according to General Method 16b using 4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (Example E-20; 0.200 g, 0.75 mmol), toluene-4-thiosulfonic acid S-[5-(tert-butyl-dimethyl-silanyloxymethyl)-2-isopropyl-thiophen-3-yl]ester (Example BB-9; 0.377 g, 0.83 mmol), NEt3 (0.209 mL, 1.50 mmol), and acetonitrile (1.5 mL). As part of the purification, the silylether was cleaved by dissolving the crude coupled product in THF (50 mL) and then treated with a 1.0 M THF solution of tetrabutylammoniumflouride (1.5 mL, 1.5 mmol). After 30 minutes, the mixture was diluted with H2O and extracted with EtOAc. The organic layers were then combined, dried (MgSO4), and concentrated. The resulting residue was then submitted to column chromatography (eluting with 3% MeOH in CH2Cl2) to provide the title compound, mp 52-54° C.

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