Diisopropyl Ether → Ethyl (E)-3-(3-bromo-1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoate

HRID 1527680Notes

Reaction equation

HRID 1527680 reaction equation
[Br:1][C:2]1[C:3]([CH:16]=O)=[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/[CH:32]=[C:33](\C)/[C:34]([O:36][CH2:37][CH3:38])=[O:35].O(C(C)C)C(C)C>>[Br:1][C:2]1[C:3](/[CH:16]=[C:33](\[CH3:32])/[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[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 3

HCID 7914Diisopropyl EtherHCID 112086483-Bromo-1,4-dimethoxy-2-naphthaldehydeHCID 46180044HCID 46180044, compound

Product 1

HCID 46180107Ethyl (E)-3-(3-bromo-1,4-dimethoxynaphthalen-2-yl)-2-methylpropenoate

Procedure

Compound 98e was prepared from 38 (0.515 g, 1.75 mmol) as described above for 28a to give 0.373 g (0.984 mmol, 56%) of the product as a white solid following flash chromatography (1:19 i-Pr2O:hexanes) and recrystallization from Et2O/hexanes. (0.314 g E; 0.059 g Z)

Workup

  1. customto give

Sources & evidence

ORD record
ord-83b9d314dd2e449789ab4e0d94cfa6b4
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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