Furan → HCID 86672886, compound

HRID 1752836Notes

Reaction equation

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

Participants

Reactant 3

HCID 8029Furan

HCID 8857Ethyl Acetate

HCID 86672883HCID 86672883, compound

Product 1

HCID 86672886HCID 86672886, compoundYield 67%

Procedure

Prepared in 67% yield (63.3 mg, 0.26 mmol) from the reaction of 2-bromo-N-(phenylmethoxy)propanamide (100.7 mg, 0.39 mmol) with furan via general procedure B. Rf=0.3 (3:1, hexanes:EtOAc); 1H-NMR (500 MHz, CDCl3): δ 7.47-7.32 (m, 5H), 6.57 (dd, J=6.2, 1.0 Hz, 1H), 6.41 (dd, J=6.0, 1.7 Hz, 1H), 5.25 (d, J=1.5 Hz, 1H), 5.00 (d, J=11.0 Hz, 1H), 4.87 (d, J=11.0 Hz, 1H), 4.85 (dd, J=5.0, 1.9 Hz, 1H), 3.17 (qd, J=7.4, 5.0 Hz, 1H), and 1.09 (d, J=7.4 Hz, 3H); 13C-NMR (126 MHz, CDCl3): δ 172.7, 136.1, 135.8, 133.8, 129.7, 128.9, 128.7, 91.6, 82.9, 78.1, 45.1, and 10.6; IR (film) 3089, 2970, 2970, 2934, 2876, 1697, 1497, 1455, 1377, 1209, 1053 cm-1; HRMS calculated for C14H16NO3 (M+H)+ 246.1125, observed 246.1118.

Sources & evidence

ORD record: ord-7b5f6b7fe1664bbe9abc677a9ee62a52
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163033B2

Reaction notes

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