(E)-3-Acetylacrylic acid methyl ester → HCID 59445852, compound

HRID 1886857Notes

Reaction equation

HRID 1886857 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]([CH3:23])/[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]([CH3:23])[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 5363720(E)-3-Acetylacrylic acid methyl esterHCID 108786402-chlorododecanal

Product 1

HCID 59445852HCID 59445852, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared according to the general procedure from 2-chlorododecanal and (E)-methyl 4-oxopent-2-enoate using 0.5 mol % 1 as the catalyst in 71% yield as a single diastereomer (white solid). [α]D20 (c 1.20, CHCl3)=+204.8; mp=40-42° C.; 1H NMR (400 MHz, CDCl3) δ 5.09 (dd, 1H, J=6.3, 1.1 Hz), 3.68 (s, 3H), 3.30 (dt, 1H, J=6.3, 1.0 Hz), 2.66 (dd, 1H, J=7.0, 6.3 Hz), 1.90 (t, 3H, J=1.0 Hz), 1.35-1.24 (m, 18H), 0.86 (t, 3H, J=6.8 Hz); 13C NMR (100 MHz, CDCl3) δ 171.4, 169.8, 152.3, 98.4, 52.5, 41.5, 40.6, 32.0, 29.7, 29.7, 29.5, 29.5, 27.3, 27.2, 22.8, 18.9, 14.3; IR (thin film) ν 3062, 2925, 2854, 1777, 1740, 1463, 1436, 1383, 1167, 1142 cm−1; HRMS (ESI) calcd for C18H30O4 [M+Na]+ 333.1996, found 333.2021; >99% ee (3S,4S)-isomer as determined by HPLC(OD-H, 20:1 hexanes/i-PrOH), tr (3S,4S)=6.7 min, tr (3R,4R)=6.0 min.

Workup

  1. customPrepared
  2. customtr (3S,4S)=6.7 min, tr (3R,4R)=6.0 min.

Sources & evidence

ORD record
ord-1ad1febccf5245e68e98c02538d005d5
Source dataset
uspto-grants-2013_08
Patent number
US08501658B2

Reaction notes

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