Diethyl Oxalate → HCID 59612098, compound

HRID 1907116Notes

Reaction equation

[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](=[O:13])[CH3:12])=[C:5]([F:14])[C:4]=1[O:15][CH3:16].[C:17](OCC)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>>[CH2:21]([O:20][C:18](=[O:19])[C:17](=[O:23])[CH2:12][C:11](=[O:13])/[CH:10]=[CH:9]/[C:6]1[CH:7]=[CH:8][C:3]([Cl:2])=[C:4]([O:15][CH3:16])[C:5]=1[F:14])[CH3:22]

Participants

Reactant 3

HCID 7268Diethyl Oxalate

HCID 5360545Sodium

HCID 59612094HCID 59612094, compound

Product 1

HCID 59612098HCID 59612098, compoundYield 93%

Procedure

Using the procedure of Example 2, sodium pellets (5.52 g, 0.24 mol), (E)-4-(4-chloro-2-fluoro-3-methoxyphenyl)-but-3-en-2-one (2; 45.73 g, 0.20 mol) and diethyl oxalate (36.54 g, 0.25 mol) were reacted to give (E)-6-(4-chloro-2-fluoro-3-methoxyphenyl-2,4-dioxo-hex-5-enoic acid ethyl ester (5; 61.1 g, 93%) as yellow crystals: mp 67.5-69° C.; 1H NMR (400 MHz, CDCl3) δ 14.71 (s, 1H), 7.78 (d, J=16.1 Hz, 1H), 7.27-7.18 (m, 2H), 6.73 (d, J=16.1 Hz, 1H), 6.54 (s, 1H), 4.38 (q, J=7.1 Hz, 2H), 3.99 (d, J=1.2 Hz, 3H), 1.41 (t, J=7.1 Hz, 3H); HRMS-ESI (m/z): calcd for C15H14ClFNO5, 328.051. found, 328.051.

Workup

customwere reacted

Sources & evidence

ORD record: ord-c325a961993e49599f662060435f0db0
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598086B2

Reaction notes

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