Butyl vinyl ether → HCID 58460780, compound

HRID 1909496Notes

Reaction equation

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

Participants

Reactant 2

HCID 8108Butyl vinyl ether

HCID 133811-Decene

Product 1

HCID 58460780HCID 58460780, compoundYield 68%

Procedure

Following the general procedure, 1-decene (50.0 mg, 0.356 mmol) was treated with butyl vinyl ether (357 mg, 3.56 mmol) and 2.5 mol % of in situ-generated complex 1a (89.0 μL, 0.10 M, 8.90 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 8b (51.2 mg, 0.241 mmol, 68.0% yield, 98% Z isomer) as a colorless oil. IR (neat): 2958(s), 2923 (s), 2854 (s), 1664 (s), 1464 (m), 1375 (m), 1306 (w), 1259 (m), 1102 (s); 1H NMR (400 MHz, CDCl3): δ [diagnostic E isomer signal: 6.21 (1H, dt, J=12.8, 1.2 Hz)], 5.91 (1H, dt, J=6.4, 1.6 Hz), 4.32 (1H, td, J=7.2, 6.2 Hz), 3.70 (2H, t, J=6.4 Hz), 2.06 (2H, tdd, J=7.2, 7.2, 1.2 Hz), 1.63-1.55 (2H, m), 1.44-1.21 (14H, m), 0.93 (3H, t, J=7.6 Hz), 0.88 (3H, t, J=7.2 Hz); 13C NMR (100 MHz, CDCl3): δ 145.0, 107.1, 72.0, 32.1, 32.0, 30.0, 29.6, 29.5, 29.4, 24.1, 22.8, 19.2, 14.3, 14.0; HRMS (ESI+) [M+H]+ calcd for C14H29O: 213.2218, found: 213.2220.

Workup

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

Sources & evidence

ORD record: ord-8bc2a042c70a47c088e902d2b68ae9b6
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598400B2

Reaction notes

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