P-Chloroacetophenone → 6-(4-Chloro-phenyl)-4-hydroxy-3-(2-isopropyl-phenylsulfanyl)-pyran-2-one

HRID 2394055Notes

Reaction equation

HRID 2394055 reaction equation
[Cl: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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:10][C:41](=[O:42])[C:40]([S:39][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[CH:30]([CH3:31])[CH3:32])=[C:44]([OH:45])[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7467P-ChloroacetophenoneHCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 19596178[(2-Isopropylphenyl)thio)propanedioic acid

Product 1

HCID 546814676-(4-Chloro-phenyl)-4-hydroxy-3-(2-isopropyl-phenylsulfanyl)-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by Method A using 4'-chloroacetophenone (2.33 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. 148°-151° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.25 (d, 6H), 3.41 (m, 1H), 6.86 (s, 1H), 6.92 (m, 1H), 7.08 (m, 2H), 7.27 (m, 1H), 7.62 (m, 2H), 7.86 (m, 2H).

Sources & evidence

ORD record
ord-c0a116e7d644411ba34a761391363091
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

Loading…