Triethylamine → 6-(1,1'-Biphenyl-3-yl)-4-hydroxy-3-[(2-isobutylphenyl)thio]-2H-pyran-2-one

HRID 613139

Reaction equation

HRID 613139 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:13](=[O:15])[CH3:14])[CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.C(N(CC)CC)C.[CH2:35]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[S:45][CH:46]([C:50](O)=[O:51])[C:47](O)=[O:48])[CH:36]([CH3:38])[CH3:37]>C(Cl)Cl>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[O:15][C:47](=[O:48])[C:46]([S:45][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=3[CH2:35][CH:36]([CH3:37])[CH3:38])=[C:50]([OH:51])[CH:14]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 2585681-((1,1'-Biphenyl)-3-yl)ethan-1-oneHCID 19596221[(2-Isobutylphenyl)thio]propanedioic acid

Product 1

HCID 547186816-(1,1'-Biphenyl-3-yl)-4-hydroxy-3-[(2-isobutylphenyl)thio]-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by Method A using 3'-phenylacetophenone (2 g, 10.20 mmol), trimethylsilyl triflate (2.27 g, 10.20 mmol), triethylamine (2.06 g, 20.40 mmol), methylene chloride (20 mL), and diethyl ester of [(2-isobutylphenyl)thio]propanedioic acid (1.14 g, 5.1 mmol). m.p. 187-188° C. 1H NMR (400 MHz, DMSO-d6) δ 0.83 (d, 6H), 1.78 (m, 1H), 2.4 (d, 2H), 7.03 (s, 1H), 7.08 (s, 4H), 7.44 (t, 1H), 7.53 (t, 2H), 7.67 (t, 1H), 7.75 (s, 1H), 7.78 (s, 1H), 7.86 (m, 2H), 8.08 (s, 1H).

Sources & evidence

ORD record
ord-ecc336529a78474e8fb4dc1c6d503f59
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Linked notes

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