Benzene, (diazomethyl)- → HCID 18358879、化合物

HRID 428441ノート

反応式

HRID 428441 の反応式
[C:1]1([CH:7]=[N+:8]=[N-:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([OH:25])[C:18]#[C:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:13]([N+:26]([O-:28])=[O:27])[CH:12]=1>C1COCC1>[C:1]1([C:7]2[C:18]([CH:17]([C:14]3[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][C:13]=3[N+:26]([O-:28])=[O:27])[OH:25])=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 136601Benzene, (diazomethyl)-HCID 18358875Ethyl 4-(4-chloro-2-nitrophenyl)-4-hydroxy-2-butynoate

生成物 1

HCID 18358879HCID 18358879、化合物収率 29.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of freshly generated phenyldiazomethane (2.44 g, 20.7 mmol) in 10 mL of anhydrous THF was added to ethyl 4-(4-chloro-2-nitrophenyl)-4-hydroxy-2-butynoate (5.86 g, 20.7 mmol) in 10 mL THF and the mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched with excess ethereal acetic acid and concentrated via rotary evaporation to an oil (12.24 g) which solidified on cooling. This was filtered to yield the title compound as a pale yellow solid (2.42 g). The filtrate was concentrated via rotary evaporation to an oil which was triturated with hexane:ethyl acetate (4:1) to yield an additional 1.52 g of the title compound (48% combined yield).

後処理

  1. customThe reaction mixture was quenched with excess ethereal acetic acid
  2. concentrationconcentrated via rotary evaporation to an oil (12.24 g) which
  3. temperatureon cooling
  4. filtrationThis was filtered

出典と根拠

ORDレコード
ord-ebd4aa3b0e114d51a7dcbb6e422f01b2
出典データセット
uspto-grants-2001_11
特許番号
US06313290B1

反応ノート

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