N-Allyl-2,2,2-trifluoroacetamide → HCID 86628469, compound

HRID 2070665Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]([OH:17])([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[CH:5]=[CH:6][CH:7]=1.[CH2:18]([NH:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[CH:19]=[CH2:20]>>[F:24][C:23]([F:26])([F:25])[C:22]([NH:21][CH2:18]/[CH:19]=[CH:20]/[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][C:10]([OH:17])([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[CH:3]=1)=[O:27]

Participants

Reactant 2

HCID 558569N-Allyl-2,2,2-trifluoroacetamide

HCID 66629554HCID 66629554, compound

Product 1

HCID 86628469HCID 86628469, compound

Procedure

4-((3-bromophenyl)ethynyl)heptan-4-ol was coupled with N-allyl-2,2,2-trifluoroacetamide following the procedure described in Example 123 to give (E)-2,2,2-trifluoro-N-(3-(3-(3-hydroxy-3-propylhex-1-ynyl)phenyl)allyl)acetamide as a pale yellow oil. Yield (0.082 g, 10%): 1H NMR (400 MHz, DMSO-d6) δ 9.68 (t, J=5.4 Hz, 1H), 7.42-7.39 (m, 2H), 7.30 (t, J=8.0 Hz, 1H), 7.23 (dt, J=7.6, 1.4 Hz, 1H), 6.51 (d, J=16.0 Hz, 1H), 6.29 (dt, J=16.0, 6.0 Hz, 1H), 5.13 (s, 1H), 3.95 (t, J=5.4 Hz, 2H), 1.60-1.40 (m, 8H), 0.89 (t, J=7.2 Hz, 6H).

Sources & evidence

ORD record: ord-9314518a828e4b23a394f57b5efbd11e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299307B2

Reaction notes

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