Methyl-4-oxo-4-phenyl-2-butenoate → HCID 15605892, compound

HRID 1886858Notes

Reaction equation

HRID 1886858 reaction equation
Cl[CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]=[O:4].[O:15]=[C:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20]>C(Cl)(Cl)Cl>[CH2:5]([C@H:2]1[C@@H:18]([C:19]([O:21][CH3:22])=[O:20])[CH:17]=[C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:15][C:3]1=[O:4])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 1484788Methyl-4-oxo-4-phenyl-2-butenoateHCID 108786402-chlorododecanal

Product 1

HCID 15605892HCID 15605892, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared according to the general procedure from 2-chlorododecanal and (E)-methyl 4-oxo-4-phenylbut-2-enoate using 0.5 mol % 1 as the catalyst in 90% yield as a single diastereomer (white solid). [α]r)20 (c 1.15, CHCl3)=+154.3; mp=108-111° C.; 1H NMR (400 MHz, CDCl3) δ 7.66-7.63 (m, 2H), 7.40-7.37 (m, 3H), 5.89 (d, 1H, J=6.4 Hz), 3.73 (s, 3H), 3.57 (t, 1H, J=6.3 Hz), 2.76 (q, 1H, J=6.3 Hz), 2.04 (t, 1H, J=7.0 Hz), 1.47-1.26 (m, 18H), 0.88 (t, 3H, J=6.8 Hz); 13C NMR (100 MHz, CDCl3) δ 171.0, 169.5, 152.4, 132.0, 129.8, 128.8, 125.0, 97.9, 52.7, 41.9, 40.7, 32.1, 29.8, 29.8, 29.6, 29.6, 27.4, 27.3, 22.9, 14.4; IR (thin film) ν 3062, 2916, 2846, 1758, 1722, 1464, 1339, 1176, 1115 cm−1; HRMS (ESI) calcd for C23H32O4 [M+Na]+ 395.2192, found 395.2192; 99% ee (3S,4S)-isomer as determined by HPLC (AD-H, 9:1 hexanes/i-PrOH), tr (3S,4S)=7.2 min, tr (3R,4R)=10.3 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-999e5be898034746a86b0b8d47d20a17
Source dataset
uspto-grants-2013_08
Patent number
US08501658B2

Reaction notes

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