Diethyl Oxalate → 5-Hexenoic acid, 6-[p-chlorophenyl]-2,4-dioxo-, ethyl ester

HRID 889645Notes

Reaction equation

[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.[C:14](OCC)(=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[O:20])[CH2:12][C:11](=[O:13])/[CH:10]=[CH:9]/[C:6]1[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=1)[CH3:19]

Participants

Reactant 3

HCID 7268Diethyl Oxalate

HCID 7365724-(4-Chlorophenyl)-3-buten-2-one

HCID 5360545Sodium

Product 1

HCID 53758255-Hexenoic acid, 6-[p-chlorophenyl]-2,4-dioxo-, ethyl esterYield 87.1%

Procedure

Using the procedure of Example 2, sodium pellets (6.33 g, 0.275 mol), (E)-4-(4-chlorophenyl)-but-3-en-2-one (45.16 g, 0.25 mol) and diethyl oxalate (43.8 g, 0.30 mol) were reacted to give (E)-6-(4-chlorophenyl-2,4-dioxo-hex-5-enoic acid ethyl ester (4; 61.1 g, 87%) as yellow crystals: mp 117-118° C.; 1H NMR (400 MHz, CDCl3) δ 14.80 (s, 1H), 7.68 (d, J=15.9 Hz, 1H), 7.53-7.35 (m, 4H), 6.62 (d, J=15.9 Hz, 1H), 6.53 (s, 1H), 4.38 (q, J=7.2 Hz, 2H), 1.40 (t, J=7.1 Hz, 3H); HRMS-ESI (m/z): calcd for C14H13ClO4, 280.050. found, 280.050.

Workup

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Sources & evidence

ORD record: ord-573786531a5b4698893af5b4829b488e
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252938B2

Reaction notes

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