Ethyl Acetate → 8-methoxycarbonyl 4H-pyrrolo[2,1-c][1,4]-benzoxazine

HRID 399839Notes

Reaction equation

HRID 399839 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[N:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:29][OH:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>O1CCCC1.O>[CH3:21][O:20][C:18]([C:17]1[CH:22]=[CH:23][C:14]2[O:30][CH2:29][C:25]3=[CH:26][CH:27]=[CH:28][N:24]3[C:15]=2[CH:16]=1)=[O:19]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18945313Methyl 4-hydroxy-3-(2-hydroxymethylpyrrol-1-yl)benzoate

Product 1

HCID 189452648-methoxycarbonyl 4H-pyrrolo[2,1-c][1,4]-benzoxazineYield 26.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (2.3 ml) was added dropwise to the mixture of methyl 4-hydroxy-3-(2-hydroxymethylpyrrol-1-yl)benzoate (2.5 g) and triphenylphosphine (4.0 g) in tetrahydrofuran (50 ml) under ice-cooling and the mixture was stirred for 2 hours at ambient temperature. The mixture was poured into the mixture of ethyl acetate and water. The separated organic layer was washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave the residue, which was purified by column chromatography on silica gel eluting with chloroform. The eluted fractions containing the desired product were collected and evaporated in vacuo to give 8-methoxycarbonyl 4H-pyrrolo[2,1-c][1,4]-benzoxazine (0.61 g).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave the residue, which
  6. customwas purified by column chromatography on silica gel eluting with chloroform
  7. additionThe eluted fractions containing the desired product
  8. customwere collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-326fc971b6994dddbb83621f4331409e
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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