Diethyl Oxalate → 2-(2-Biphenyl-4-yl-furan-5-yl)-2-oxoacetic acid ethyl ester

HRID 2300001Notes

Reaction equation

[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)=[CH:3][CH:2]=1.[C:18](OCC)(=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>>[CH2:22]([O:21][C:19](=[O:20])[C:18]([C:9]1[O:8][C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:2][CH:3]=2)=[CH:11][CH:10]=1)=[O:24])[CH3:23]

Participants

Reactant 2

HCID 7268Diethyl Oxalate

HCID 110422552-Biphenyl-4-yl-furan

Product 1

HCID 183415122-(2-Biphenyl-4-yl-furan-5-yl)-2-oxoacetic acid ethyl esterYield 74%

Procedure

According to the procedure described in Example 13 for the preparation of 1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3′-yl)ethane-1,2-dione, 2-biphenyl-4-yl-furan was deprotonated and alkylated with diethyl oxalate to give in 74% yield 2-(2-biphenyl-4-yl-furan-5-yl)-2-oxoacetic acid ethyl ester as a yellow solid, mp 91-94° C. 1H NMR: δ 7.94 (d, 2H, J=8.5 Hz), 7.83 (d, 1H, J=4.1 Hz), 7.69 (d, 2H, J=8.1 Hz), 7.64 (d, 2H, J=7.7 Hz), 7.47 (t, 2H, J=7.4 Hz), 7.39 (t, 1H, J=7.2 Hz), 6.90 (d, 1H, J=4.2 Hz), 4.44 (q, 2H, J=7.0 Hz), 1.45 (t, 3H, J=7.2 Hz). Anal. Calculated for C20H16O4: C, 74.99; H, 5.03. Found: C, 75.1 1; H, 5.07.

Sources & evidence

ORD record: ord-aee33ae8a2534e6b95b8be086e3e9605
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495699B2

Reaction notes

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