Potassium Carbonate → 3-(2-tert-Butyl-4-hydroxymethyl-5-methylphenylsulfanyl)-4-hydroxy-6,6-bis[2-(3-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one

HRID 356550Notes

Reaction equation

HRID 356550 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)[O:5][C:4](=[O:26])[CH:3]=1.[C:27]([C:31]1[CH:36]=[C:35]([CH2:37][OH:38])[C:34]([CH3:39])=[CH:33][C:32]=1[S:40]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:27]([C:31]1[CH:36]=[C:35]([CH2:37][OH:38])[C:34]([CH3:39])=[CH:33][C:32]=1[S:40][C:3]1[C:4](=[O:26])[O:5][C:6]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)[CH2:7][C:2]=1[OH:1])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10499026S-[2-Tert-butyl-4-(hydroxymethyl)-5-methylphenyl] 4-methylbenzenesulfonothioateHCID 546822904-Hydroxy-6,6-bis-[2-(3-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Product 1

HCID 546823113-(2-tert-Butyl-4-hydroxymethyl-5-methylphenylsulfanyl)-4-hydroxy-6,6-bis[2-(3-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound was synthesized following General Method 9 and using 172 mg (0.5 mmol) of 4-hydroxy-6,6-bis-[2-(3-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example XX), 179 mg (0.5 mmol) of toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl) ester (prepared in Example FFF), 270 mg (2.0 mmol) of K2CO3, and 2 mL of DMF. The reaction was worked up as described and chromatographed on silica get eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH), to yield the title compound, m.p. 92°-94° C. 1H NMR (DMSO-d6) δ 1.48 (s, 9 H), 1.80 (s, 3 H), 2,07 (m, 4 H), 2.6 (m, 4 H), 3.0 (s, 2 H), 4.35 (s, 2 H), 6.6 (m, 6 H), 6.65 (s, 1 H), 7.05 (t, 2 H), 7.25 (s, 1 H), 9.25 (s, 2 H).

Workup

  1. customThe compound was synthesized
  2. customchromatographed on silica
  3. customget
  4. washeluting with (1:1 CH2Cl2 :EtOAc+2% MeOH)

Sources & evidence

ORD record
ord-a957de5e394b47c3969abe26e3c3ae92
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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