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

HRID 399839ノート

反応式

HRID 399839 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-326fc971b6994dddbb83621f4331409e
出典データセット
uspto-grants-1998_10
特許番号
US05824691

反応ノート

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