Potassium Carbonate → 5-{[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl]sulfanyl}-2-cyclohexyl-6-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2,3-dihydro-4h-pyran-4-one

HRID 356540Notes

Reaction equation

HRID 356540 reaction equation
[CH:1]1([C:7]2([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[O:12][C:11](=[O:13])[CH:10]=[C:9]([OH:14])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:24]([C:28]1[CH:33]=[C:32]([CH2:34][OH:35])[C:31]([CH3:36])=[CH:30][C:29]=1[S:37]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:27])([CH3:26])[CH3:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:24]([C:28]1[CH:33]=[C:32]([CH2:34][OH:35])[C:31]([CH3:36])=[CH:30][C:29]=1[S:37][C:10]1[C:11](=[O:13])[O:12][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:8][C:9]=1[OH:14])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10499026S-[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl] 4-methylbenzenesulfonothioateHCID 547203146-Cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Product 1

HCID 546822675-{[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl]sulfanyl}-2-cyclohexyl-6-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2,3-dihydro-4h-pyran-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as described in General Method 9 from 6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example NN; 156 mg, 0.499 mmol), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl) ester (prepared in Example FFF; 250 mg, 0.546 mmol), K2CO3 (303 mg, 2.195 mmol), and DMF (4 mL). The reaction was stirred at room temperature for 2.5 hours and then worked up in the usual manner. The crude product was flash chromatographed using CH2Cl2 : MeOH (98:2) to give the desired product as a solid, m.p. 138°-139° C. (dec.). 1H NMR (CDCl3) δ 1.0-2.1 (m, 13 H), 1.58 (s, 9 H), 2.03 (s, 3 H), 2.6-2.7 (m, 3 H), 3.05 (d, 1 H), 4.6 (s, 2 H), 6.69-6.74 (d, s, 3 H), 6.98 (d, 2 H), 7.34 (s, 1 H), 7.74 (s, 1 H).

Workup

  1. customThe title compound was prepared
  2. customchromatographed

Sources & evidence

ORD record
ord-5e135a867089498eb1a488adc6ddcddd
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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