2-Bromoethanol → HCID 85844223, compound

HRID 520790Notes

Reaction equation

HRID 520790 reaction equation
[CH3:1][N:2]([CH3:32])[C:3](=[O:31])[O:4][C:5]1[CH:10]=[CH:9][C:8](/C=C/C(=O)CC(=O)/C=C/C2C=CC(O)=C(OC)C=2)=[CH:7][C:6]=1[O:29][CH3:30].BrCCO.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:32][N:2]([CH3:1])[C:3](=[O:31])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:29][CH3:30]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 715062464-((1E,6E)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dien-1-yl)-2-methoxyphenyl dimethylcarbamate

Product 1

HCID 85844223HCID 85844223, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 4-((1E,6E)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dien-1-yl)-2-methoxyphenyl dimethylcarbamate (88 mg, 0.2 mmol, 1.0 eq), 2-bromoethanol (37.5 mg, 0.3 mmol, 1.5 eq) and K2CO3 (110 mg, 0.8 mmol, 4.0 eq) in acetone (10 ml) was stirred under reflux for 5 h. Then the mixture was concentrated and The resulting residue was separated by Prep-HPLC to provide 4-41E,6E)-7-(4-(2-hydroxyethoxy)-3-methoxyphenyl)-3,5-dioxohepta-1,6-dien-1-yl)-2-methoxyphenyl dimethylcarbamate (35 mg, 36.1%). LRMS (M+H+) m/z calculated 484.2. found 484.2. 1H NMR (CDCl3, 400 MHz) δ 7.58-7.62 (dd, 2H), 7.07-7.13 (m, 5H), 6.91 (d, 1H), 6.48-6.56 (m, 2H), 5.83 (s, 1H), 4.14-4.17 (t, 2H), 3.96-3.99 (t, 2H), 3.91 (s, 3H), 3.88 (s, 3H), 3.13 (s, 3H), 3.02 (s, 3H).

Workup

  1. temperatureunder reflux for 5 h
  2. concentrationThen the mixture was concentrated
  3. customThe resulting residue was separated by Prep-HPLC

Sources & evidence

ORD record
ord-5e0e3d49d2734b01ad475a04c1e47377
Source dataset
uspto-grants-2016_05
Patent number
US09328081B2

Reaction notes

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