Propargyl bromide → Formamide, N-[2-[3-methoxy-4-(2-propynyloxy)phenyl]ethyl]-

HRID 1841637Notes

Reaction equation

HRID 1841637 reaction equation
C[O-].[Na+].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][CH:14]=[O:15])=[CH:7][C:6]=1[O:16][CH3:17].[CH2:18](Br)[C:19]#[CH:20]>CO>[CH3:17][O:16][C:6]1[CH:7]=[C:8]([CH2:11][CH2:12][NH:13][CH:14]=[O:15])[CH:9]=[CH:10][C:5]=1[O:4][CH2:20][C:19]#[CH:18]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10942334Sodium MethoxideHCID 11389958N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]formamide

Product 1

HCID 11379286Formamide, N-[2-[3-methoxy-4-(2-propynyloxy)phenyl]ethyl]-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium methoxide (32 ml of a 5.4 M solution in methanol, 0.17 mol) is added to a solution of N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-formamide (32 g, 0.16 mol) in methanol (400 ml). Propargyl bromide (20 g, 0.17 mol) is added and the mixture is refluxed for 4 hours. After evaporation the residue is taken up in ethyl acetate (400 ml) and washed with water (2×200 ml). The organic layer is dried over magnesium sulfate and evaporated. The residue is submitted to flash-chromatography to give the N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-formamide. 1H-NMR (300 MHz, CDCl3): 2.44 (t, 1H, C≡CH), 2.73 (t, 2H, CH2CH2), 3.51 (t, 2H, CH2CH2), 3.82 (s, 3H, OCH3), 4.69 (m, 2H, OCH2), 5.53 (bs, 1H, NH), 6.62-6.95 (m, 3H, CH arom.), 8.09 (s, 1H, CHO).

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. customAfter evaporation the residue
  3. washwashed with water (2×200 ml)
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-f6b7f13930174dc7bbd8df5e8382cd82
Source dataset
uspto-grants-2004_01
Patent number
US06683211B1

Reaction notes

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