반응 #2358493

ord-c985030f22484b65a5990c8fd3b0d2bc

반응 방정식

[Cl-].[Cl-].[Mg+2]
magnesium chloride
CC1=CC(O/C=C2/C(=O)N(C(=O)OC(C)(C)C)C3C=CCC23)OC1=O
tert-butyl (3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylene]-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]pyrrole-1-carboxylate
ClCCl
CH2Cl2
CC1=CC(O/C=C2/C(=O)NC3C=CCC23)OC1=O
desired compound
수율 40.0%
CC1=CC(O/C=C2/C(=O)NC3C=CCC23)OC1=O
(3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylene]-1,3a,4,6a-tetrahydrocyclopenta[b]pyrrol-2-one
수율 40.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    여과filtrated
  2. 2
    농축concentrated
  3. 3
    기타purified by flash chromatography (EtOAc

실험 절차

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+).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09119398B2uspto-grants-2015_09