1-Octene → HCID 86706736, compound

HRID 2170129Notes

Reaction equation

[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)=[N+]=[N-].[CH2:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>>[CH2:16]([CH:15]1[CH2:14][N:1]1[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

Reactant 2

HCID 81251-Octene

HCID 108993811-azido-4-(trifluoromethyl)benzene

Product 1

HCID 86706736HCID 86706736, compound

Procedure

1-azido-4-(trifluoromethyl)-benzene (0.392 g, 2.09 mmol), 1-octene (3.575 g, 31.9 mmol), and [(Me,EtTCPh)Fe(NCCH3)2](PF6)2 (0.0029 g, 0.0021 mmol) were used in the General Catalytic Reaction described above yielding 0.212 g, 37.3%. 1H NMR (CDCl3, 499.74 MHz): δ 7.47 (d, J=8.0 Hz, 2H), 7.03 (d, J=8.0 Hz, 2H), 2.13 (m, 2H), 2.09 (d, J=6.0 Hz, 1H), 1.58 (m, 4H), 1.41 (m, 2H), 1.34 (m, 4H), 0.92 (t, J=6.5 Hz, 3H). 13C NMR (CDCl3, 125.66 MHz): δ 158.40, 126.27 (q, J=3.8 Hz), 124.60 (q, J=270.0 Hz), 124.19 (q, J=32.7 Hz), 120.83, 40.55, 34.23, 33.16, 31.97, 29.32, 27.71, 22.75, 14.18. 19F NMR (CDCl3, 470.2 MHz): δ −61.7. GC/MS (m/z): 271.1. DART HR MS (m/z): [M+H]+272.1609 (found). C15H21F3N, 272.1626 (calcd).

Workup

customabove yielding 0.212 g, 37.3%

Sources & evidence

ORD record: ord-9ddfedcb12234124a7ad1071dc81310c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050589B2

Reaction notes

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