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

HRID 356561Notes

Reaction equation

HRID 356561 reaction equation
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)[O:11][C:10](=[O:12])[CH:9]=[C:8]([OH:13])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23]([C:27]1[CH:32]=[C:31]([CH2:33][OH:34])[C:30]([CH3:35])=[CH:29][C:28]=1[S:36]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:26])([CH3:25])[CH3:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:23]([C:27]1[CH:32]=[C:31]([CH2:33][OH:34])[C:30]([CH3:35])=[CH:29][C:28]=1[S:36][C:9]1[C:10](=[O:12])[O:11][C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)[CH2:7][C:8]=1[OH:13])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10499026S-[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl] 4-methylbenzenesulfonothioateHCID 547203236-Cyclopentyl-4-hydroxy-6-[2-(3-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Product 1

HCID 547131835-[2-tert-butyl-4-(hydroxymethyl)-5-methyl-phenyl]sulfanyl-2-cyclopentyl-4-hydroxy-2-[2-(3-hydroxyphenyl)ethyl]-3H-pyran-6-oneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as described in General Method 9 using 6-cyclopentyl-4-hydroxy-6-[2-(3-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (0.26 g, 0.9 mmol) from Example AAAAA, toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl) ester (prepared in Example FFF; 0.35 g, 1.0 mmol), 0.54 g (3.9 mmol) of K2CO3 in DMF (10 mL). The product was purified by column chromatography on silica gel eluting with EtOAc:hexane:CH2Cl2 (1:1:1) to afford the product in 81% yield as a white solid (m.p. 172°-174° C.). 1H-NMR (DMSO-d6) δ 1.47 (s, 9 H), 1.4-1.7 (m, 8 H, 1.9 (s, 3 H), 1.95-2.1 (m, 2 H), 2.35 (t, 1 H), 2.5-2.6 (m, 2 H, partially obscured by DMSO), 2.7 (q, 2 H), 4.35 (s, 2 H), 4.95 (bs, 1 H), 6.55 (t, 3 H), 6.65 (s, 1 H), 7.05 (t, 1 H), 7.25 (s, 1 H), 9.25 (s, 1 H).

Workup

  1. customThe product was purified by column chromatography on silica gel eluting with EtOAc:hexane:CH2Cl2 (1:1:1)

Sources & evidence

ORD record
ord-f835c03dd3444d46bd90cec04b6258fc
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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