1-Decene → HCID 86706735, compound

HRID 2170128Notes

Reaction equation

HRID 2170128 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[N+]=[N-])=[CH:3][CH:2]=1.[CH2:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>>[CH2:13]([CH:12]1[CH2:11][N:7]1[C:4]1[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 133811-Decene2×HCID 1374301-Azido-4-methylbenzene2×

Product 1

HCID 86706735HCID 86706735, compound

Procedure

0.1% catalyst loading: p-Tolyl azide (0.240 g, 1.81 mmol), 1-decene (7.410 g, 52.8 mmol), and [(Me,EtTCPh)Fe(NCCH3)2](PF6)2 (0.0025 g, 0.0018 mmol) were used in the General Catalytic Reaction described above yielding 0.312 g, 70.4%. 1% catalyst loading: p-Tolyl azide (0.103 g, 0.773 mmol), 1-decene (2.223 g, 15.8 mmol), and [(Me,EtTCPh)Fe(NCCH3)2](PF6)2 (0.0107 g, 0.0077 mmol) were used in the General Catalytic Reaction described above yielding 0.156 g, 82.1%. 1H NMR (CDCl3, 499.74 MHz): δ 7.03 (d, J=7.5 Hz, 2H), 6.89 (d, J=7.0 Hz, 2H), 2.28 (s, 3H), 2.03 (m, 3H), 1.59 (m, 4H), 1.40 (m, 2H), 1.31 (m, 8H), 0.91 (t, J=6.0 Hz, 3H). 13C NMR (CDCl3, 125.66 MHz): δ 152.77, 131.45, 129.51, 120.65, 40.33, 34.17, 33.41, 32.02, 29.74, 29.69, 29.42, 27.85, 22.80, 20.78, 14.24. GC/MS (m/z): 245.2. DART HR MS (m/z): [M+H]+246.2211 (found). C17H28N, 246.2222 (calcd).

Workup

  1. customabove yielding 0.312 g, 70.4%
  2. customabove yielding 0.156 g, 82.1%

Sources & evidence

ORD record
ord-3b267a5bef8c4e8cb9adfc78bb4e241a
Source dataset
uspto-grants-2015_06
Patent number
US09050589B2

Reaction notes

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