Methane, dichloromethoxy- → HCID 86636834, compound

HRID 548985Notes

Reaction equation

HRID 548985 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH2:11][N:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][CH2:14][C:15]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:21][O:22]C(Cl)Cl>C(Cl)Cl.O>[CH:21]([C:6]1[C:7]2[C:15]3[CH2:14][CH2:13][N:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][C:10]=3[O:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:22]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 66592542HCID 66592542, compound

Product 1

HCID 86636834HCID 86636834, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 8-methoxy-3,4-dihydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate (from step 5) (0.264 g, 0.96 mmol), in methylene chloride, was added stannic chloride (0.424 g, 1.6 mmol) and 1,1-dichloromethyl methyl ether (0.1655 g, 1.4 mmol) at −10° C. Reaction mass was diluted with dichloromethane, water was added to it and organic layer was thoroughly washed with water after separation. It was concentrated and purified to yield Ethyl 5-formyl-8-methoxy-3,4-dihydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate (97%).

Workup

  1. customReaction mass
  2. additionwas added to it and organic layer
  3. washwas thoroughly washed with water
  4. customafter separation
  5. concentrationIt was concentrated
  6. custompurified

Sources & evidence

ORD record
ord-9d17e7ee91834493ba65e5d2e0ff112d
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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