Ethyl 3-methylcinnamate → HCID 86709745, compound

HRID 2174612Notes

Reaction equation

[I-].[CH:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:4])[CH3:3].[CH3:24][C:25]1[CH:26]=[C:27]([CH:35]=[CH:36][CH:37]=1)[CH:28]=[CH:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[CH3:3][C:2]1([CH3:4])[C@@H:28]([C:27]2[CH:26]=[C:25]([CH3:24])[CH:37]=[CH:36][CH:35]=2)[C@@H:29]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

Reactant 2

HCID 589327Ethyl 3-methylcinnamate

HCID 2723783Isopropyltriphenylphosphonium iodide

Product 1

HCID 86709745HCID 86709745, compoundYield 75.3%

Procedure

Isopropyltriphenylphosphonium iodide (17.3 g, 40 mmol) and ethyl 3-methylcinnamate (7.6 g, 40 mmol) were reacted as described under General Procedure B to furnish the title compound (7.0 g, 75%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.17 (t, J=7.4 Hz, 1H), 7.03-6.95 (m, 3H), 4.18 (q, J=7.2 Hz, 2H), 2.66 (d, J=5.8 Hz, 1H), 2.33 (s, 3H), 1.93 (d, J=5.8 Hz, 1H), 1.38 (s, 3H), 1.30 (t, J=7.2 Hz, 3H), 0.93 (s, 3H).

Sources & evidence

ORD record: ord-c16bf29cb0b14c2e96bee0370d427c3b
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062013B2

Reaction notes

Loading…