Butyl vinyl ether → HCID 58460745, compound

HRID 1909495Notes

Reaction equation

[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:2]=[CH2:3].C([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=C>>[CH2:13]([O:12]/[CH:3]=[CH:2]\[CH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:14][CH2:15][CH3:16]

Participants

Reactant 2

HCID 8108Butyl vinyl ether

HCID 9309Allylbenzene

Product 1

HCID 58460745HCID 58460745, compoundYield 76.1%

Procedure

Following the general procedure for enol ether cross metathesis, allyl benzene (50.0 mg, 0.423 mmol, 7) was treated with butyl vinyl ether (424 mg, 4.23 mmol), 2.5 mol % of in situ-generated complex 1a (106 μL, 0.10 M, 10.6 μmol; final substrate concentration=4.0 M), and allowed to stir for 2 h. The unpurified product is 98% Z (as determined by 400 MHz 1H NMR analysis). The resulting brown oil was purified by neutral alumina chromatography (100% hexanes) to afford 8a (61.3 mg, 0.322 mmol, 76.0% yield, >98% Z isomer) as a colorless oil. The physical and spectral data were identical to those previously reported for compound 8a.9 IR (neat): 3028 (w), 2959 (m), 2933 (m), 2872 (m), 1663 (s), 1495 (m), 1453 (m), 1373 (m), 1253 (m), 1108 (s); 1H NMR (400 MHz, CDCl3): δ 7.32-7.16 (5H, m), [diagnostic E isomer signal: 6.37 (1H, dt, J=16.0, 1.2 Hz)], 6.08 (1H, dt, J=6.0, 1.6 Hz), 4.57 (1H, td, J=7.6, 6.2 Hz), 3.79 (2H, t, J=6.4 Hz), 3.45 (2H, d, J=7.6 Hz), 1.69-1.61 (2H, m), 1.49-1.39 (2H, m), 0.97 (3H, t, J=7.6 Hz); 13C NMR (100 MHz, CDCl3): δ 145.7, 142.1, 128.4, 128.4, 125.8, 105.4, 72.2, 32.0, 30.4, 19.2, 14.0; HRMS (ESI+) [M+H]+ calcd for C13H19O: 191.1436, found: 191.1432.

Workup

customThe resulting brown oil was purified by neutral alumina chromatography (100% hexanes)

Sources & evidence

ORD record: ord-7c7db702976f4396bcd450c72d9143ca
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598400B2

Reaction notes

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