3-Methylacetophenone → HCID 54681484, compound

HRID 2393998Notes

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][C:17]1[CH:18]=[C:19]([C:23](=O)[CH3:24])[CH:20]=[CH:21][CH:22]=1.[K+].[Br-]>>[OH:15][C:13]1[CH:24]=[C:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([CH3:16])[CH:18]=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

Reactant 3

HCID 114553-Methylacetophenone

HCID 253877Potassium Bromide

HCID 19596125[(Phenylmethyl)thio]propanedioic acid

Product 1

HCID 54681484HCID 54681484, compoundYield 65%

Procedure

This compound was prepared by the condensation of the diethyl ester of [(phenylmethyl)thio]-propanedioic acid (1 g, 3.54 mmol) with the corresponding trimethylsilyl enol ether of 3'-methyl acetophenone (7.09 mmol, 1.46 g) as described in general procedure A. Isolated Yield: 65% m.p. 137°-138° C. 1H NMR (400 MHz, DMSO-d6) δ 11.9 (brs, 1 H), 7.6 (m, 2 H), 7.39 (t, 1 H), 7.35 (d, 1 H), 7.25 (d, 4 H), 7.2 (m, 1 H), 6.7 (s, 1 H), 4.0 (s, 2 H), 2.38 (s, 3 H); IR (KBr) 3030, 2585, 1617, 1536, 1402,. 1100, 787, 696 cm-1; MS (CI) m/e 325 (65), 291 (2), 233 (4), 119 (9), 91 (100).

Workup

customIsolated Yield: 65% m.p. 137°-138° C

Sources & evidence

ORD record: ord-40c69de4e923476f95bf69ced42df67c
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05808062

Reaction notes

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