Butyl vinyl ether → HCID 67362818, compound

HRID 1909498Notes

Reaction equation

[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=C>>[CH2:14]([O:13]/[CH:3]=[CH:2]\[CH2:1][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:15][CH2:16][CH3:17]

Participants

Reactant 2

HCID 8108Butyl vinyl ether

HCID 68525N-Allylaniline

Product 1

HCID 67362818HCID 67362818, compoundYield 52.3%

Procedure

Following the general procedure, N-allylaniline (50.0 mg, 0.375 mmol) was treated with butyl vinyl ether (376 mg, 3.75 mmol) and 5 mol % of in situ-generated complex 1a (188 μL, 0.10 M, 18.7 μmol; final substrate concentration=2.0 M) and allowed to stir for 4 h. The unpurified product is 96% Z (as determined by 400 MHz 1H NMR analysis). The resulting oil was purified by silica gel chromatography (50:1 hexanes:Et2O) to afford 8e (40.2 mg, 0.196 mmol , 52.0% yield, 96% Z isomer) as a light yellow oil. IR (neat): 3410 (br), 3048 (w), 2958 (m), 2932 (m), 2871 (m), 1660 (m), 1601 (s), 1503 (s), 1467 (m), 1431(w), 1375 (m), 1314 (m), 1250 (m), 1108 (s), 1094 (s), 1040 (m), 745 (s), 691 (s); 1H NMR (400 MHz, CDCl3): ™ δ 7.19-7.14 (2H, m), 6.72-6.67 (1H, m), 6.66-6.62 (2H, m), [diagnostic E isomer signal: 6.51 (1H, d, J=12.8 Hz)], 6.08 (1H, dt, J=6.4, 1.4 Hz), 4.51 (1H, td, J=6.6, 6.4 Hz), 3.82-3.74 (1H, m), 3.81 (2H, dd, J=6.8, 1.2 Hz), 3.79 (2H, t, J=6.4 Hz), 1.67-1.59 (2H, m), 1.47-1.37 (2H, m), 0.95 (3H, t, J=7.4 Hz); 13C NMR (100 MHz, CDCl3): ™ δ 148.5, 147.4, 129.3, 117.4, 113.2, 103.5, 72.6, 38.6, 32.0, 19.2, 14.0; HRMS (ESI+) [M+H]+ calcd for C13H20NO: 206.1545, found: 206.1541.

Workup

customThe resulting oil was purified by silica gel chromatography (50:1 hexanes:Et2O)

Sources & evidence

ORD record: ord-7676bebac78e49c2bc085e423573e0cc
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598400B2

Reaction notes

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