HCID 59648542, compound → HCID 59648667, compound

HRID 1363296Notes

Reaction equation

HRID 1363296 reaction equation
[OH:1][CH2:2][C:3]1[C:7]2[NH:8][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][C:6]=2[O:5][CH:4]=1>C(Cl)Cl.O=[Mn]=O>[CH:2]([C:3]1[C:7]2[NH:8][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][C:6]=2[O:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 59648542HCID 59648542, compound

Product 1

HCID 59648667HCID 59648667, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-hydroxymethyl-4H-furo[3,2-b]pyrrole-5-carboxylate (1.1 g, 5.26 mmol) in CH2Cl2 (100 mL) was added MnO2 (4.6 g, 52.6 mmol). The reaction mixture was stirred at rt overnight and was then filtered through Celite® and washed with CH2Cl2 (3×50 mL). The organic solution was concentrated in vacuo and chromatographed over silica gel (0 to 40% EtOAc in heptane over 30 min) to give ethyl 3-formyl-4H-furo[3,2-b]pyrrole-5-carboxylate (1.0 g, 92%) as light yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.41 (t, J=7.13 Hz, 3-H) 4.40 (q, J=7.13 Hz, 2H) 6.83 (dd, J=1.54, 1.00 Hz, 1H) 7.23 (d, J=0.88 Hz, 1H) 8.98 (br. s., 1H) 9.67 (s, 1H).

Workup

  1. filtrationwas then filtered through Celite®
  2. washwashed with CH2Cl2 (3×50 mL)
  3. concentrationThe organic solution was concentrated in vacuo
  4. customchromatographed over silica gel (0 to 40% EtOAc in heptane over 30 min)

Sources & evidence

ORD record
ord-8218a22fea8b474b85d8acac1937e683
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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