Butyl vinyl ether → (Z)-Phenyl 5-butoxypent-4-enoate

HRID 1040317Notes

Reaction equation

[C:1]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].C([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=C>>[CH2:17]([O:16]/[CH:5]=[CH:4]\[CH2:3][CH2:2][C:1]([O:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:6])[CH2:18][CH2:19][CH3:20]

Participants

Reactant 2

HCID 8108Butyl vinyl ether

HCID 15255467Phenyl pent-4-enoate

Product 1

HCID 58460847(Z)-Phenyl 5-butoxypent-4-enoateYield 79%

Procedure

Following the general procedure, phenyl pent-4-enoate (50.0 mg, 0.284 mmol) was treated with butyl vinyl ether (284 mg, 2.84 mmol) and 2.5 mol % of in situ-generated complex la (71.0 μL, 0.10 M, 7.09 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 oil was purified by silica gel chromatography (50:1 hexanes:Et2O) to afford 8c (55.6 mg, 0.224 mmol, 79.0% yield, >98% Z isomer) as a colorless oil. IR (neat): 3040 (w), 2959 (m), 2933 (m), 2872 (m), 1759 (s), 1663 (m), 1594 (m), 1493 (m), 1374 (m), 1359 (m), 1272 (m), 1227 (m), 1195 (s), 1162 (s), 1130 (s), 1102 (s), 1072 (m); 1H NMR (400 MHz, CDCl3): δ 7.40-7.34 (2H, m), 7.25-7.19 (1H, m), 7.11-7.07 (2H, m), [diagnostic E isomer signal: 6.37 (1H, d, J=12.8 Hz)], 6.02 (1H, dt, J=6.0, 1.2 Hz), 4.43 (1H, td, J=6.8, 6.4 Hz), 3.75 (2H, t, J=6.4 Hz), 2.66-2.60 (2H, m), 2.56-2.49 (2H, m), 1.65-1.57 (2H, m), 1.46-1.35 (2H, m), 0.94 (3H, t, J=7.4 Hz); 13H NMR (100 MHz, CDCl3): δ 172.0, 150.9, 146.4, 129.4, 125.7, 121.7, 103.8, 72.2, 34.7, 32.0, 19.9, 19.1, 13.9; HRMS (ESI+) [M+H]+ calcd for C15H21O3: 249.1491, found: 249.1500.

Workup

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

Sources & evidence

ORD record: ord-9e4c45aad0854fff91660e4e18f653f8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552242B2

Reaction notes

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