4'-Methoxyacetophenone → 4-Hydroxy-3-(2-isopropyl-phenylsulfanyl)-6-(4-methoxy-phenyl)-pyran-2-one

HRID 2394052Notes

Reaction equation

HRID 2394052 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.C(N(CC)CC)C.[CH:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[S:40][CH:41]([C:45](O)=[O:46])[C:42](O)=[O:43])([CH3:33])[CH3:32]>C(Cl)Cl>[OH:46][C:45]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:11][C:42](=[O:43])[C:41]=1[S:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH:31]([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 74764'-MethoxyacetophenoneHCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 19596178[(2-Isopropylphenyl)thio)propanedioic acid

Product 1

HCID 546812264-Hydroxy-3-(2-isopropyl-phenylsulfanyl)-6-(4-methoxy-phenyl)-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by Method A using 4'-methoxyacetophenone (2.26 g, 15.1 mmol), trimethylsilyl triflate (3.5 mL, 18.1 mmol), triethylamine (4.26 mL, 30.6 mmol), methylene chloride (30 mL), and diethyl ester of [(2-isopropylphenyl)thio]propanedioic acid (3.11 g, 10.0 mmol) m.p. 221°-223° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.25 (d, 6H), 3.40 (m, 1H), 3.85 (s, 3H), 6.78 (s, 1H), 6.92 (m, 1H), 7.10 (m, 4H), 7.27 (m, 1H), 7.81 (d, 2H), 12.38 (brs, 1H).

Sources & evidence

ORD record
ord-3d5a17e090ae468fac2e88c974c739f9
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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