(E)-3-(1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoic acid → (E)-3-(3-chloro-1,4-dimethoxynaphthalen-2-yl)-2-propylpropenoic acid

HRID 1527686Notes

Reaction equation

HRID 1527686 reaction equation
[Cl:1][C:2]1[C:3](/[CH:16]=[C:17](\[CH2:23][CH2:24][CH3:25])/[C:18]([O:20]CC)=[O:19])=[C:4]([O:14][CH3:15])[C:5]2[C:10]([C:11]=1[O:12][CH3:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.COC1C2C(=CC=CC=2)C(OC)=CC=1/C=C(\C)/C(O)=O>CCOC(C)=O>[Cl:1][C:2]1[C:3](/[CH:16]=[C:17](\[CH2:23][CH2:24][CH3:25])/[C:18]([OH:20])=[O:19])=[C:4]([O:14][CH3:15])[C:5]2[C:10]([C:11]=1[O:12][CH3:13])=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 46180242(E)-3-(1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoic acidHCID 70834972Ethyl (E)-3-(3-chloro-1,4-dimethoxynaphthalen-2-yl)-2-propylpropenoate

Product 1

HCID 68772573(E)-3-(3-chloro-1,4-dimethoxynaphthalen-2-yl)-2-propylpropenoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound 42b was prepared from 41b (0.028 g, 0.077 mmol) as described above for 29a to give 0.026 g (0.077 mmol, 100%) of the product as a red solid following flash chromatography (1:3 EtOAc:hexanes 0.5% AcOH) and recrystallization from Et2O/hexanes.

Workup

  1. customto give

Sources & evidence

ORD record
ord-59cd4acffe254bf69ecb2e7d6d0c8d71
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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