Ethanol → Ethyl alpha-Azido-beta-(4-methoxypyrid-3-yl)-acrylate

HRID 1445919Notes

Reaction equation

HRID 1445919 reaction equation
C([N:8]1[C:16]2C=[CH:14][CH:13]=[C:12]([OH:17])[C:11]=2[CH:10]=C1C)C1C=CC=CC=1.[N:19]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N+:20]=[N-:21].[CH3:28]CO>>[N:19]([C:22](=[CH:10][C:11]1[CH:16]=[N:8][CH:14]=[CH:13][C:12]=1[O:17][CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N+:20]=[N-:21]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 69480Acetic acid, azido-, ethyl esterHCID 107523601-Benzyl-2-methyl-1H-indol-4-ol

Product 1

HCID 72796408Ethyl alpha-Azido-beta-(4-methoxypyrid-3-yl)-acrylate

Procedure

A homogeneous mixture of 3-formyl-4-methoxypyridine 1 (7.0 g, 54.7 mmol) and ethyl azidoacetate (5.0 g, 36.4 mmol) in anhydrous EtOH (50 mL) was added through a dropping funnel to a well-stirred solution containing Na (0.1.24 g, 54.7 mmol) in anhydrous EtOH (30 mL) under N2 at −15° C. The mixture was stirred at that temperature for 4 h. During this time the precipitated solid was filtered and washed with ice cooled ethanol (30 mL). The compound was dried under vacuum oven for 3 h to get pure title compound 2 as white crystalline solid. Mp 92-95° C.; Yield: 4.8 g, 53%; ESI MS: m/z 248.9 (M+1).

Workup

  1. additionwas added through a dropping funnel to a well-stirred solution
  2. filtrationDuring this time the precipitated solid was filtered
  3. washwashed with ice
  4. temperaturecooled ethanol (30 mL)
  5. customThe compound was dried under vacuum oven for 3 h

Sources & evidence

ORD record
ord-b6f355069f22498385b55c06fcbebe06
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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