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

HRID 382203Notes

Reaction equation

C([C@H]1COC(C)(C)N1C(=O)C(C1C=CN(C2C=CC(C3C=CC=CC=3)=CC=2)C=1)=O)C1C=CC=CC=1.[C:36]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:41]=[CH:40][C:39]([C:42]2[O:43][CH:44]=[CH:45][CH:46]=2)=[CH:38][CH:37]=1.[C:53](OCC)(=[O:59])[C:54]([O:56][CH2:57][CH3:58])=[O:55]>>[CH2:57]([O:56][C:54](=[O:55])[C:53]([C:44]1[O:43][C:42]([C:39]2[CH:40]=[CH:41][C:36]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)=[CH:37][CH:38]=2)=[CH:46][CH:45]=1)=[O:59])[CH3:58]

Participants

Reactant 3

HCID 7268Diethyl Oxalate

HCID 110422552-Biphenyl-4-yl-furan

HCID 183412581-(4(S)-benzyl-2, 2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)ethane-1, 2-dione

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.

Sources & evidence

ORD record: ord-b1a250579bdc4bbabf4506fc78284347
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06306892B1

Reaction notes

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