1-Methylcyclohexene → HCID 86706738, compound

HRID 2170132Notes

Reaction equation

HRID 2170132 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[N+]=[N-])=[CH:3][CH:2]=1.[CH3:11][C:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1>>[CH3:11][C:12]12[N:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=3)[CH:17]1[CH2:16][CH2:15][CH2:14][CH2:13]2

Participants

3

Reactant 2

HCID 115741-MethylcyclohexeneHCID 1374301-Azido-4-methylbenzene

Product 1

HCID 86706738HCID 86706738, compound

Procedure

p-Tolyl azide (0.100 g, 0.751 mmol), 1-methyl-cyclohexene (4.055 g, 42.2 mol), and [(Me,EtTCPh)Fe(NCCH3)2](PF6)2 (0.0104 g, 0.0075 mmol) were used in the General Catalytic Reaction described above yielding 0.059 g, 39%. 1H NMR (CDCl3, 499.74 MHz): δ 7.02 (d, J=7.5 Hz, 2H), 6.75 (d, J=6.5 Hz, 2H), 2.28 (s, 3H), 2.15 (m, 1H), 2.02 (m, 1H), 1.99 (m, 2H), 1.64 (m, 1H), 1.55 (m, 2H), 1.35 (m, 1H), 1.25 (m, 1H), 0.99 (s, 3H) 13C NMR (CDCl3, 125.66 MHz): δ 148.74, 130.52, 129.27, 120.49, 44.17, 41.60, 32.41, 24.62, 21.16, 20.85, 20.81, 20.65. GC/MS (m/z): 201.1. DART HR MS (m/z): [M+H]+202.1594 (found). C15H22N, 202.1596 (calcd).

Workup

  1. customabove yielding 0.059 g, 39%

Sources & evidence

ORD record
ord-edd89d6fa2354c4d9e0f57bf55afaa63
Source dataset
uspto-grants-2015_06
Patent number
US09050589B2

Reaction notes

Loading…