1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl 3-methyl-1H-pyrrole-2-carboxylate

HRID 1434789ノート

反応式

HRID 1434789 の反応式
[CH2:1]([O:3][C:4]([CH:6]1[C:10]([CH3:11])=[CH:9][CH2:8][N:7]1S(C1C=CC(C)=CC=1)(=O)=O)=[O:5])[CH3:2].C1CCN2C(=NCCC2)CC1>C1COCC1.CCOCC>[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[CH:9][C:10]=1[CH3:11])=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15747141Ethyl 3-methyl-1-(4-methylphenyl)sulfonyl-2,5-dihydropyrrole-2-carboxylate

生成物 1

HCID 5324582Ethyl 3-methyl-1H-pyrrole-2-carboxylate収率 98.6%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Pyrroline 83 (8.80 g, 28.48 mmol) was dissolved in THF (70 mL). DBU (9.78 mL, 65.50 mmol) was added dropwise and the resulting solution stirred under reflux overnight. The mixture was cooled to room temperature, diluted with ether and washed with 5% aq. HCl, 5% sodium bicarbonate solution and water. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to give the crude solid 84 (4.30 g, 98%). 1H-NMR (400 MHz, CDCl3): δ 1.37 (t, 3H), 2.35 (s, 3H), 4.31 (q, 2H), 6.08 (d, 1H), 6.81 (d, 1H), 8.90 (s broad, 1H) ppm. 13C-NMR (100 MHz, CDCl3): δ□ 12.76, 14.53, 59.96, 112.58□, 119.35, 121.53, 127.96, 162.01 ppm. DEPT (100 MHz, CDCl3): CH3 carbons: 12.76, 14.53; CH2 carbons: 59.96; CH carbons: 112.58, 121.53 ppm. LC/MS: 90.74%, m/z=153.

後処理

  1. temperatureunder reflux overnight
  2. washwashed with 5% aq. HCl, 5% sodium bicarbonate solution and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-454237d05cf946ba9397c3942859a283
出典データセット
uspto-grants-2009_11
特許番号
US07615572B2

反応ノート

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