Propanal → (2S,3R)-3-(4-methoxyphenyl)-2-methyl-4-nitrobutanal

HRID 1500159Notes

Reaction equation

HRID 1500159 reaction equation
[CH:1](=[O:4])[CH2:2][CH3:3].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[N+:15]([O-:17])=[O:16])=[CH:9][CH:8]=1.CC(O)C.CCCCCC>C(Cl)(Cl)Cl>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C@H:13]([CH2:14][N+:15]([O-:17])=[O:16])[C@H:2]([CH3:3])[CH:1]=[O:4])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 527PropanalHCID 3776IsopropanolHCID 8058HexaneHCID 697963trans-4-Methoxy-beta-nitrostyrene

Product 1

HCID 58500177(2S,3R)-3-(4-methoxyphenyl)-2-methyl-4-nitrobutanal

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared from propionaldehyde and (E)-1-methoxy-4-(2-nitrovinyl)benzene according to the general procedure. Both enantiomeric excess and diastereomeric ratio were determined by HPLC with an AS-H column at 230 nm (2-propanol:hexane=5:95), 1.0 mL/min; major enantiomer tmajor=42.10 min, minor enantiomer tminor=60.77 min. [α]D20=−4.6 (c=1.3, CHCl3).

Workup

  1. customtmajor=42.10 min, minor enantiomer

Sources & evidence

ORD record
ord-48895fa851dd4012ad2bb0540bef8ba0
Source dataset
uspto-grants-2015_12
Patent number
US09206090B2

Reaction notes

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