Potassium Carbonate → 5-[2-tert-butyl-4-(2-hydroxyethoxy)-5-methyl-phenyl]sulfanyl-4-hydroxy-2,2-bis[2-(4-hydroxy-3-methoxy-phenyl)ethyl]-3H-pyran-6-one

HRID 1003906Notes

Reaction equation

HRID 1003906 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([O:28][CH3:29])[CH:22]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:17][CH3:18])[CH:11]=2)[O:5][C:4](=[O:30])[CH:3]=1.[C:31]([C:35]1[CH:40]=[C:39]([O:41][CH2:42][CH2:43][O:44][Si](C(C)(C)C)(C)C)[C:38]([CH3:52])=[CH:37][C:36]=1[S:53]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:34])([CH3:33])[CH3:32].C([O-])([O-])=O.[K+].[K+].NC1C=CC(CCC(=O)CCC2C=CC(N)=CC=2)=CC=1>CN(C=O)C>[C:31]([C:35]1[CH:40]=[C:39]([O:41][CH2:42][CH2:43][OH:44])[C:38]([CH3:52])=[CH:37][C:36]=1[S:53][C:3]1[C:4](=[O:30])[O:5][C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:17][CH3:18])[CH:11]=2)([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([O:28][CH3:29])[CH:22]=2)[CH2:7][C:2]=1[OH:1])([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 10791774Toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl}esterHCID 540520781,5-Bis (4-amino-phenyl)-pentan-3-oneHCID 546822754-Hydroxy-6,6-bis-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Product 1

HCID 546822815-[2-tert-butyl-4-(2-hydroxyethoxy)-5-methyl-phenyl]sulfanyl-4-hydroxy-2,2-bis[2-(4-hydroxy-3-methoxy-phenyl)ethyl]-3H-pyran-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound was prepared using General Method 9 and the following quantities: 100 mg (0.24 mmol) of 4-hydroxy-6,6-bis-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example QQ), 123 mg (0.24 mol) of toluene-4-thiosulfonic acid S-{2-tert-butyl-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-phenyl} ester (prepared in Example PPP), 133 mg (0.96 mmol) of K2CO3, and 10 mL of DMF. The reaction was worked up by addition of 10 mL 1. ON HCl and stirring for 10 minutes, followed by extraction with EtOAc. The organic layer was dried (Na2SO4), concentrated, and chromatographed on silica gel, eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH), to give the title compound, m.p. 76-82° C. 1H NMR (DMSO-d6) δ 1.5 (s, 9 H), 1.75 (s, 3 H), 2.05 (m, 4 H), 2.6 (m, 4 H), 2.95 (s, 2 H), 3.7 (m, 8 H), 3.95 (t, 2 H), 4.8 (br s, 1 H), 6.65 (m, 7 H), 7.0 (s, 1 H), 8.75 (s, 2 H).

Workup

  1. customThe compound was prepared
  2. extractionfollowed by extraction with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed on silica gel
  6. washeluting with (1:1 CH2Cl2 :EtOAc+2% MeOH)

Sources & evidence

ORD record
ord-d0be714c6e04473896454ca2adc775cd
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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