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 1003894Notes

Reaction equation

HRID 1003894 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-493a9f5edb9e40f3aa98a51f2005a2bf
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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