Potassium Carbonate → 5-[2-tert-butyl-4-(hydroxymethyl)-5-methyl-phenyl]sulfanyl-4-hydroxy-2-isopropyl-2-[2-(3-thienyl)ethyl]-3H-pyran-6-one

HRID 23506Notes

Reaction equation

HRID 23506 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH:15]([CH3:17])[CH3:16])([CH2:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[O:5][C:4](=[O:18])[CH:3]=1.[C:19]([C:23]1[CH:28]=[C:27]([CH2:29][OH:30])[C:26]([CH3:31])=[CH:25][C:24]=1[S:32]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:19]([C:23]1[CH:28]=[C:27]([CH2:29][OH:30])[C:26]([CH3:31])=[CH:25][C:24]=1[S:32][C:3]1[C:4](=[O:18])[O:5][C:6]([CH:15]([CH3:16])[CH3:17])([CH2:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[CH2:7][C:2]=1[OH:1])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10499026S-[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl] 4-methylbenzenesulfonothioateHCID 546770164-Hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one

Product 1

HCID 546770255-[2-tert-butyl-4-(hydroxymethyl)-5-methyl-phenyl]sulfanyl-4-hydroxy-2-isopropyl-2-[2-(3-thienyl)ethyl]-3H-pyran-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as described in General Method 16a using 4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (Example E-20; 0.84 mmol), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester (Example BB-2; 0.92 mmol), potassium carbonate (3.35 mmol) in DMF (4 mL). The product was purified via flash chromatography over silica gel eluting with 10:90 EtOAc:CH2Cl2, mp 63-70° C. MS (APCI): 475 (M+H).

Workup

  1. customThe product was purified via flash chromatography over silica gel eluting with 10:90 EtOAc

Sources & evidence

ORD record
ord-6e6225832ba34be29e20313a0ae08f42
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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