Isopropanol → (S)-3-(4-Methoxyphenyl)-2,2-dimethyl-4-nitrobutanal

HRID 1500167Notes

Reaction equation

HRID 1500167 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[N+:11]([O-:13])=[O:12])=[CH:5][CH:4]=1.[CH:14](=[O:18])[CH:15]([CH3:17])[CH3:16].CC(O)C.CCCCCC>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]([CH2:10][N+:11]([O-:13])=[O:12])[C:15]([CH3:17])([CH3:16])[CH:14]=[O:18])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6561IsobutyraldehydeHCID 8058HexaneHCID 697963trans-4-Methoxy-beta-nitrostyrene

Product 1

HCID 58500180(S)-3-(4-Methoxyphenyl)-2,2-dimethyl-4-nitrobutanal

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared from trans-1-methoxy-4-(2-nitrovinyl) benzene and isobutyraldehyde according to general method. The enantiomeric excess was determined by HPLC with Chiralpak AS-H column at 210 nm (2-propanol:hexane=20:80), 1 ml/min; tmajor=12.7 min, tminor=15.8 min, [α]D20=+9.1 (c=1.2, CHCl3);

Workup

  1. customtmajor=12.7 min

Sources & evidence

ORD record
ord-84c25fab80e04e8c8e4269c611c26f1d
Source dataset
uspto-grants-2015_12
Patent number
US09206090B2

Reaction notes

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