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

HRID 399839노트

반응식

HRID 399839 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-326fc971b6994dddbb83621f4331409e
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05824691

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