Formaldehyde → HCID 66592542, compound

HRID 548984Notes

Reaction equation

HRID 548984 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13][NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1.C=O.[C:22]1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]3[CH2:22][N:14]([C:15]([O:16][CH2:17][CH3:18])=[O:19])[CH2:13][CH2:12][C:8]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 66592500HCID 66592500, compound

Product 1

HCID 66592542HCID 66592542, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl 2-(7-methoxy-1-benzofuran-3-yl)ethylcarbamate (from step 4) (0.649 g, 2.5 mmol), paraformaldehyde (0.150 g, 5.0 mmol) and 4-toluene sulphonic acid (0.0475 g, 0.125 mmol) was subjected to Dean-Stark for 2-3 hrs. After cooling to RT, water was added and organic layer was separated dried over anhy. sodium sulphate and concentrated. On purification on silica gel, it yielded ethyl 8-methoxy-3,4-dihydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate (96%).

Workup

  1. customorganic layer was separated
  2. customdried over anhy
  3. concentrationsodium sulphate and concentrated
  4. customOn purification on silica gel, it

Sources & evidence

ORD record
ord-03c3ff2a2197462f85acf7d5ebecd350
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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