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

HRID 23503Notes

Reaction equation

HRID 23503 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][C:8]2([CH:16]([CH3:18])[CH3:17])[O:13][C:12](=[O:14])[CH:11]=[C:10]([OH:15])[CH2:9]2)=[CH:2]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:11]1[C:12](=[O:14])[O:13][C:8]([CH2:7][CH2:6][C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)([CH:16]([CH3:18])[CH3:17])[CH2:9][C:10]=1[OH:15])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10499026S-[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl] 4-methylbenzenesulfonothioateHCID 54688331HCID 54688331, compound

Product 1

HCID 546761075-[2-tert-butyl-4-(hydroxymethyl)-5-methyl-phenyl]sulfanyl-2-[2-(3-furyl)ethyl]-4-hydroxy-2-isopropyl-3H-pyran-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as described in General Method 16a using 6-(2-furan-3-yl-ethyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one (Example E-18; 1 mmol), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl)ester (Example BB-2; 1.1 mmol), potassium carbonate (4 mmol) in DMF (4 mL). The product was flash chromatographed over silica gel using 70:20:10 hexane:EtOAc:CH2Cl2, mp 62-70° C. MS (APCI): 457 (M−H).

Workup

  1. customchromatographed over silica gel using 70:20:10 hexane

Sources & evidence

ORD record
ord-54a0ea22665d4e7082cba9ddebb15481
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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