Methane, dichloromethoxy- → HCID 86636831, compound

HRID 548978Notes

Reaction equation

HRID 548978 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]2[O:12][C:13]3[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=3[C:8]=2[CH2:7]1)=[O:5])[CH3:2].Cl[CH:22]([O:24]C)Cl>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9]2[O:12][C:13]3[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]([CH:22]=[O:24])[C:14]=3[C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 66592354HCID 66592354, compound

Product 1

HCID 86636831HCID 86636831, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-ethyoxycarbonyl-6-methoxy-1,2,3,4-tetrahydro[1]benzofuro[3,2-c]pyridine (from step 7) (0.420 g, 1.52 mmol) was dissolved in dichloromethane (25 ml). To this stannic chloride (0.675 g, 2.59 mmol) was added followed by addition of dichloromethylmethylether (0.17 g, 1.52 mmol) at −10° C. and stirred for 30 min. Reaction was quenched by pouring on crushed ice and extracted with ethyl acetate. Ethyl acetate layer was washed with water (10 ml×2), brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography using 100-200 mesh silica gel and eluted in 10% ethyl acetate in petroleum ether to get 170 mg of the product as white solid.

Workup

  1. customReaction
  2. customwas quenched
  3. additionby pouring
  4. customon crushed ice
  5. extractionextracted with ethyl acetate
  6. washEthyl acetate layer was washed with water (10 ml×2), brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography
  10. washeluted in 10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-f6e98292d4d34dd6991a9b543251b9ba
Source dataset
uspto-grants-2011_05
Patent number
US07943634B2

Reaction notes

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