Diethyl Oxalate → Ethyl 4-[4-(methylthio)phenyl]-2,4-dioxobutanoate

HRID 476101Notes

Reaction equation

HRID 476101 reaction equation
[Na].[CH3:2][S:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[C:13](OCC)(=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>>[CH3:2][S:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH2:11][C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 7268Diethyl OxalateHCID 745011-(4-(Methylthio)phenyl)ethan-1-oneHCID 5360545Sodium

Product 1

HCID 10539688Ethyl 4-[4-(methylthio)phenyl]-2,4-dioxobutanoate

Procedure

The title compound was prepared in the same manner as for intermediate 66 using sodium metal (0.160 g, 6.95 mmol), 1-[4-(methylthio)phenyl]ethanone (1.05 g, 6.32 mmol) and diethyl ethanedioate (0.856 mL, 6.32 mmol). The product was collected as 1.58 g (59%). LCMS E-S (M+H)=266.9. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.29-1.50 (m, 3H), 2.41-2.62 (m, 3H), 4.23-4.49 (m, 2H), 7.15-7.38 (m, 2H), 7.89 (dd, J=8.72, 2.15 Hz, 2H).

Workup

  1. customThe product was collected as 1.58 g (59%)

Sources & evidence

ORD record
ord-678b3faf83fa41ba86818a98a57bf91c
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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