Reaktion #51785

ord-5d1424b694814559be749bfd223acce8

Reaktionsgleichung

CCOC(C)=O
EtOAc
CC(C)C1(CCc2cccs2)CC(O)=CC(=O)O1
4-hydroxy-6-isopropyl-6-(2-thiophen-2-yl-ethyl)-5,6-dihydro-pyran-2-one
Cc1ccc(S(=O)(=O)Sc2cc(C)c(CO)cc2C(C)(C)C)cc1
toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
Cc1cc(SC2=C(O)CC(CCc3cccs3)(C(C)C)OC2=O)c(C(C)(C)C)cc1CO
title compound
Cc1cc(SC2=C(O)CC(CCc3cccs3)(C(C)C)OC2=O)c(C(C)(C)C)cc1CO
3-(2-tert-Butyl-4-hydroxymethyl-5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-6-(2-thiophen-2-yl-ethyl)-5,6-dihydro-pyran-2-one

Edukte

CCOC(C)=O
EtOAc
CC(C)C1(CCc2cccs2)CC(O)=CC(=O)O1
4-hydroxy-6-isopropyl-6-(2-thiophen-2-yl-ethyl)-5,6-dihydro-pyran-2-one
Cc1ccc(S(=O)(=O)Sc2cc(C)c(CO)cc2C(C)(C)C)cc1
toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2
CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The title compound was prepared as described in General Method 16a using 4-hydroxy-6-isopropyl-6-(2-thiophen-2-yl-ethyl)-5,6-dihydro-pyran-2-one (Example E-21; 1 mmol), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester (Example BB-2; 1.2 mmol), potassium carbonate (4 mmol) in DMF (3 mL). The product was isolated via flash chromatography over silica gel using 10:90 EtOAc:CH2Cl2, mp 73-77° C. MS (APCI): 475 (M+H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06852711B2uspto-grants-2005_02