(E)-3-Acetylacrylic acid methyl ester → HCID 59445861, compound

HRID 1886852Notes

Reaction equation

HRID 1886852 reaction equation
Cl[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][CH2:5][CH:6]=[O:7].[O:12]=[C:13]([CH3:20])/[CH:14]=[CH:15]/[C:16]([O:18][CH3:19])=[O:17]>C(Cl)(Cl)Cl>[CH2:4]([C@H:5]1[C@@H:15]([C:16]([O:18][CH3:19])=[O:17])[CH:14]=[C:13]([CH3:20])[O:12][C:6]1=[O:7])[C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:2]=1

Participants

4

Reactant 2

HCID 5363720(E)-3-Acetylacrylic acid methyl esterHCID 218597263-(2-Chlorophenyl)propanal

Product 1

HCID 59445861HCID 59445861, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared according to the general procedure from 2-chloro-hydrocinnamaldehyde and (E)-methyl 4-oxopent-2-enoate using 0.5 mol % 1 as the catalyst in 88% yield as a single diasteromer (colorless oil). [α]D20 (c 1.10, CHCl3)=+218.7; 1H NMR (400 MHz, CDCl3) δ 7.32-7.23 (m, 3H), 7.12 (d, 2H, J=7.2 Hz), 5.02 (d, 1H, J=7.2 Hz), 3.73 (s, 3H), 3.48 (dd, 1H, J=14.3, 4.6 Hz), 3.02 (t, 1H, J=6.0 Hz), 2.89-2.84 (m, 1H), 2.66 (dd, 1H, J=14.3, 10.1 Hz), 1.89 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 171.3, 169.3, 152.6, 138.3, 129.2, 129.0, 127.0, 98.7, 52.6, 42.8, 40.3, 33.4, 19.0; IR (thin film) ν 3062, 2954, 1780, 1732, 1496, 1435, 1362, 1164 cm−1; HRMS (ESI) calcd for C15H16O4 [M+Na]+ 283.0940, found 283.0944; 99% ee (3S,4S)-isomer as determined by HPLC (AD-H, 9:1 hexanes/i-PrOH), tr (3S,4S)=12.0 min, tr (3R,4R)=9.40 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a2283ca0c9b744caadbcd3989a985f34
Source dataset
uspto-grants-2013_08
Patent number
US08501658B2

Reaction notes

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