Dichloromethane → HCID 117970158, compound

HRID 2271311Notes

Reaction equation

HRID 2271311 reaction equation
[CH3:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([O:8]/[CH:9]=[C:10]2\[CH:11]3[CH2:25][CH:24]=[CH:23][CH:12]3[N:13](C(OC(C)(C)C)=O)[C:14]\2=[O:15])[CH:3]=1.[Cl-].[Mg+2].[Cl-].C(Cl)Cl>C(#N)C>[CH3:1][C:2]1[C:6](=[O:7])[O:5][CH:4]([O:8]/[CH:9]=[C:10]2\[CH:11]3[CH2:25][CH:24]=[CH:23][CH:12]3[NH:13][C:14]\2=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 5360315Magnesium ChlorideHCID 117970121HCID 117970121, compound

Product 1

HCID 117970158HCID 117970158, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl (3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylene]-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]pyrrole-1-carboxylate Ib-1 (28 mg, 0.080 mmol) in acetonitrile (1 mL) was stirred with magnesium chloride (23 mg, 0.24 mmol) at 40° C. for 7 h. The solution was then diluted into CH2Cl2, filtrated, concentrated and purified by flash chromatography (EtOAc, then 5% MeOH in CH2Cl2) giving the desired compound as a colorless oil (8 mg, 40%); 1H NMR (400 MHz, CDCl3) 7.27 (1H, s), 6.93 (1H, s), 6.54 (1H, brs), 6.14 (1H, s), 5.87 (1H, d), 5.71 (1H, brs), 4.65 (1H, d), 3.66 (1H, m), 2.83 (1H, m), 2.46 (1H, d), 2.02 (3H, s): LCMS (Method A): 0.63 min; ES+270 (M+Na+).

Workup

  1. filtrationfiltrated
  2. concentrationconcentrated
  3. custompurified by flash chromatography (EtOAc

Sources & evidence

ORD record
ord-c985030f22484b65a5990c8fd3b0d2bc
Source dataset
uspto-grants-2015_09
Patent number
US09119398B2

Reaction notes

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