Reaction #51783

ord-75a2aace05ba4d729d244f264ae1219b

Reaction equation

CC(C)C1(CCC2CCCO2)CC(O)=CC(=O)O1
4-hydroxy-6-isopropyl-6-[2-(tetrahydro-furan-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(CCC3CCCO3)(C(C)C)OC2=O)c(C(C)(C)C)cc1CO
title compound
Cc1cc(SC2=C(O)CC(CCC3CCCO3)(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-(tetrahydro-furan-2-yl)-ethyl]-5,6-dihydro-pyran-2-one

Reactants

CC(C)C1(CCC2CCCO2)CC(O)=CC(=O)O1
4-hydroxy-6-isopropyl-6-[2-(tetrahydro-furan-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

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherFlash chromatographed over silica gel using 10:90 EtOAc

Procedure

The title compound was prepared as described in General Method 16a using 4-hydroxy-6-isopropyl-6-[2-(tetrahydro-furan-2-yl)-ethyl]-5,6-dihydro-pyran-2-one (Example E-19; 0.98 mmol), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester (Example BB-; 1.18 mmol), potassium carbonate (3.93 mmol) in DMF (5 mL). Flash chromatographed over silica gel using 10:90 EtOAc:CH2Cl2, mp 57-59° C. MS (APCI): 461 (M−H).

Source

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