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

HRID 1527697Notes

Reaction equation

HRID 1527697 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)=[C:5]([CH3:15])[C:4]=1/[CH:16]=[C:17](\[CH2:21][CH2:22][CH2:23][CH3:24])/[C:18]([OH:20])=[O:19].C1(=O)C2C(=CC=CC=2)C(=O)C=C1/C=C(\C)/C(O)=O>CCOCC>[CH3:15][C:5]1[C:6](=[O:13])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3](=[O:2])[C:4]=1/[CH:16]=[C:17](\[CH2:21][CH2:22][CH2:23][CH3:24])/[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 25235423(E)-3-(1,4-Naphthoquinon-2-yl)-2-methylpropenoic acidHCID 68769894(E)-3-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-2-butylpropenoic acid

Product 1

HCID 25235470(E)-3-(3-methyl-1,4-naphthoquinon-2-yl)-2-butylpropenoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound 35b was prepared from 99b (0.148 g, 0.45 mmol) as described above for 30a to give 0.050 g (0.17 mmol, 37%) of the product as a yellow solid following flash chromatography (2:3 Et2O:hexanes 0.5% AcOH) and recrystallization from Et2O/hexanes.

Workup

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Sources & evidence

ORD record
ord-e0b0da3331b643d38803df80b0f413b9
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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