1-(4-Methoxy-3-methylphenyl)ethan-1-one → 3-Benzylsulfanyl-4-hydroxy-6-(4-methoxy-3-methyl-phenyl)pyran-2-one

HRID 613076Notes

Reaction equation

HRID 613076 reaction equation
[C:1]1([CH2:7][S:8][CH:9]([C:13]([OH:15])=O)[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=O)[CH3:25])=[CH:20][C:19]=1[CH3:27].[K+].[Br-]>CCOCC>[OH:15][C:13]1[CH:25]=[C:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[C:19]([CH3:27])[CH:20]=2)[O:12][C:10](=[O:11])[C:9]=1[S:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 248061-(4-Methoxy-3-methylphenyl)ethan-1-oneHCID 253877Potassium BromideHCID 19596125[(Phenylmethyl)thio]propanedioic acid

Product 1

HCID 546814983-Benzylsulfanyl-4-hydroxy-6-(4-methoxy-3-methyl-phenyl)pyran-2-oneYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

This compound is prepared by the condensation of diethyl ester of [(phenylmethyl)thio]propanedioic acid (1 g, mmol) with the corresponding trimethylsilylenol ether of 4'-methoxy-3'-methylacetophenone as described in general procedure A. Isolated Yield: 68%. m.p. 159-106° C. 1H NMR (400 MHz, CDCl3) δ7.67 (dd, 1 H), 7.61 (s, 1 H), 7.2 (m, 5 H), 6.8 (d, 1 H), 6.38 (s, 1 H), 3.96 (s, 2 H), 3.89 (s, 3 H), 2.25 (s, 3 H); IR (KBr) 3432, 2945, 1613, 1507, 1402, 1262, 1142, 1030, 812, 704 cm-1; MS (CI) m/e 355 (78.3), 263 (19.6), 235 (11.8), 149 (12.7), 91 (100); Analysis calc'd for: C, 67.78; H, 5.12; found: C, 67.35; H, 5.17.

Workup

  1. customIsolated Yield: 68%

Sources & evidence

ORD record
ord-352af50a16794ed4aadd59328f77ba59
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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