(E)-3-(1,4-Naphthoquinon-2-yl)-2-methylpropenoic acid → (E)-3-(1,4-naphthoquinon-2-yl)-2-propylpropenoic acid

HRID 1527695Notes

Reaction equation

HRID 1527695 reaction equation
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13]C)=[CH:5][C:4]=1/[CH:15]=[C:16](\[CH2:20][CH2:21][CH3:22])/[C:17]([OH:19])=[O:18].C1(=O)C2C(=CC=CC=2)C(=O)C=C1/C=C(\C)/C(O)=O>CCOCC>[C:3]1(=[O:2])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[CH:5]=[C:4]1/[CH:15]=[C:16](\[CH2:20][CH2:21][CH3:22])/[C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 25235423(E)-3-(1,4-Naphthoquinon-2-yl)-2-methylpropenoic acidHCID 68740428(E)-3-(1,4-dimethoxynaphthalen-2-yl)-2-propylpropenoic acid

Product 1

HCID 68772941(E)-3-(1,4-naphthoquinon-2-yl)-2-propylpropenoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound 30b was prepared from 29b (0.193 g, 0.643 mmol) as described above for 30a to give 0.064 g (0.24 mmol, 37%) of the product as a yellow solid following flash chromatography (2:3 Et2O:hexanes 0.5% AcOH) and recrystallization from Et2O/hexanes. (0.064 g E; 0.006 g Z methyl ester)

Workup

  1. customto give

Sources & evidence

ORD record
ord-54e3b48b6cae47dbab8a1439318f6eda
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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