2,2,2-Trifluoroethanol → HCID 89077467, compound

HRID 1752840Notes

Reaction equation

HRID 1752840 reaction equation
Br[C:2]([CH3:15])([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].CCOC(C)=O.[CH2:22]([OH:27])[C:23]([F:26])([F:25])[F:24]>O1C=CC=C1>[CH3:14][C:2]([O:27][CH2:22][C:23]([F:26])([F:25])[F:24])([CH3:15])[C:3]([NH:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 8857Ethyl AcetateHCID 86672885HCID 86672885, compound

Product 1

HCID 89077467HCID 89077467, compound

Reagents, catalysts & solvents 1

HCID 8029FuranSolvent

Procedure

Produced as a by-product 56% from the reaction of 2-bromo-2-methyl-N-(phenylmethoxy)propanamide with TEA in furan and trifluoroethanol. Rf=0.26 (3:1, hexanes:EtOAc); 1H NMR (500 MHz, CDCl3) δ 8.88 (s, 1H), 7.56-7.31 (m, 5H), 4.94 (s, 2H), 3.68 (q, J=8.3 Hz, 2H), 1.43 (s, 6H); 13C NMR (125 MHz, CDCl3) 13C NMR (101 MHz, cdcl3) δ 170.8, 134.9, 129.4, 129.0, 128.7, 123.7 (q, J=278 Hz), 80.4, 78.3, 61.6 (q, J=35 Hz), and 23.6; FT-IR 3218 (br), 3036; 2942, 2886, 1663 (st), 1430, 1455, 1485, 1386, 1369, 1307, 1285, 1217, 1181, 1145, 1029, 1010 cm-1; HR-ESIMS calculated for C13H17F3NO3 (M+H)+ 292.1155, observed 292.1160.

Workup

  1. customProduced as a by-product 56%

Sources & evidence

ORD record
ord-74b7b66cdbed447db2574717a23d98fe
Source dataset
uspto-grants-2015_10
Patent number
US09163033B2

Reaction notes

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