Furan → HCID 131733645, compound

HRID 1752839Notes

Reaction equation

Cl[CH:2]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:3]([NH:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[O:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[CH3:26]COC(C)=O>>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C@@H:2]2[C@@H:26]3[C:25](=[O:21])[C@H:24]([CH:23]=[CH:22]3)[N:5]([O:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:3]2=[O:4])=[CH:15][CH:16]=1

Participants

Reactant 3

HCID 8029Furan

HCID 8857Ethyl Acetate

HCID 53328668HCID 53328668, compound

Product 1

HCID 131733645HCID 131733645, compoundYield 53%

Procedure

Prepared in 53% yield (54.4 mg, 0.16 mmol) from the reaction of 2-choro-2-(4-chlorophenyl)-N-(phenylmethoxy)acetamide (95.5 mg, 0.31 mmol) with furan via general procedure B. Rf=0.48 (3:1, hexanes:EtOAc); 1H-NMR (500 MHz, CDCl3): δ 7.50-7.44 (m, 2H), 7.44-7.34 (m, 3H), 7.28 (ABd, J=8.5 Hz, 2H), 7.05 (ABd, J=8.5 Hz, 2H), 6.55 (dd, J=6.0, 1.1 Hz, 1H), 6.19 (dd, J=6.0, 1.7 Hz, 1H), 5.36 (d, J=1.3 Hz, 1H), 5.05 (d, J=11.0 Hz, 1H), 4.96 (d, J=11.0 Hz, 1H), 4.94 (dd, J=5.3, 1.8 Hz, 1H), and 4.38 (d, J=5.3 Hz, 1H); 13C-NMR (126 MHz, CDCl3): δ 169.7, 136.0, 136.0, 135.6, 133.8, 133.8, 132.0, 131.1, 129.83, 129.1, 128.8, 128.7, 91.8, 91.8, 83.1, 83.1, 78.3, and 56.5; IR (film) 3089, 3064, 3031, 2924, 1688, 1492, 1454, 1368, 1275, 1260, 1211, 1091, 1059, 1017 cm-1. HR-ESIMS: calculated for C19H17ClNO3 (M+H)+ 342.0891, observed 342.0886.

Sources & evidence

ORD record: ord-1abe129ad4364726a6d2d6ff4aa452ef
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163033B2

Reaction notes

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