4'-Hydroxyacetophenone → 4-Hydroxy-6-(4-hydroxy-phenyl)-3-(2-isopropyl-phenylsulfanyl)-pyran-2-one

HRID 2394047Notes

Reaction equation

HRID 2394047 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.C(N(CC)CC)C.[CH:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[S:39][CH:40]([C:44](O)=[O:45])[C:41](O)=[O:42])([CH3:32])[CH3:31]>C(Cl)Cl>[OH:45][C:44]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[O:10][C:41](=[O:42])[C:40]=1[S:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[CH:30]([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 74694'-HydroxyacetophenoneHCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 19596178[(2-Isopropylphenyl)thio)propanedioic acid

Product 1

HCID 547186824-Hydroxy-6-(4-hydroxy-phenyl)-3-(2-isopropyl-phenylsulfanyl)-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by Method A using 4'-hydroxyacetophenone (0.657 g, 4.83 mmol), trimethylsilyl triflate (2.05 mL, 10.62 mmol), triethylamine (2.69 mL, 19.32 mmol), methylene chloride (20 mL), and diethyl ester of [(2-isopropylphenyl)thio]propanedioic acid (1.00 g, 3.22 mmol) m.p. 250° C.; (dec.) ; 1H NMR (400 MHz, DMSO-d6) δ 1.24 (d, 6H), 3.40 (m, 1H), 6.70 (s, 1H), 6.90 (t, 3H), 7.05 (t, 1H), 7.10 (t, 1H), 7.26 (d, 1H), 7.70 (d, 2H).

Sources & evidence

ORD record
ord-fe09231eeebe4aed8b6cc8decc3f8349
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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