Methane, dichloromethoxy- → HCID 19759475, compound

HRID 248374Notes

Reaction equation

HRID 248374 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[CH:15][CH:14]=[C:13]2[C:17]#[N:18])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH:24]([O:26]C)Cl>ClCCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([CH:24]=[O:26])[CH:14]=[C:13]2[C:17]#[N:18])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 21004Methane, dichloromethoxy-2×HCID 6451240Aluminum(III) ChlorideHCID 19759220HCID 19759220, compound

Product 1

HCID 19759475HCID 19759475, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a mixture of 1-(4-ethoxycarbonylphenyl)pyrrole-2-carbonitrile (5.16 g) and aluminum chloride (5.72 g) in 1,2-dichloroethane (51 ml) was added a solution of dichloromethylmethyl ether (2.97 g) in 1,2-dichloroethane (5 ml) in one portion at -15° C. The mixture was stirred for one hour at the same temperature and then dichloromethylmethyl ether (0.6 g) was added therein. After stirring for 3 hours at 5° C., the reaction mixture was quenched with 10% hydrochloric acid. The separated organic layer was washed with 10% hydrochloric acid three times, dried, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted by 1% methanol in dichloromethane to yield 1-(4-ethoxycarbonylphenyl)-4-formylpyrrole-2-carbonitrile (2.96 g) as a pale yellow solid.

Workup

  1. stirringAfter stirring for 3 hours at 5° C.
  2. customthe reaction mixture was quenched with 10% hydrochloric acid
  3. washThe separated organic layer was washed with 10% hydrochloric acid three times
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluted by 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-8d4f14b9dbcd4f4a9ec8906d88215bb6
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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