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Chlorotrimethylsilane → p-Nitrobenzyl 2-diazo-3-trimethylsilyloxy-3-butenoate

HRID 1460729
ノート
印刷プレビュー

反応式

HRID 1460729 の反応式
[N+:1](=[C:3]([C:17]([CH3:19])=[O:18])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:5])=[N-:2].[Br-].[Li+].C(N(CC)CC)C.[CH3:29][Si:30](Cl)([CH3:32])[CH3:31]>C(#N)C>[N+:1](=[C:3]([C:17]([O:18][Si:30]([CH3:32])([CH3:31])[CH3:29])=[CH2:19])[C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)=[O:5])=[N-:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 82050Lithium BromideHCID 53872938HCID 53872938、化合物

生成物 1

HCID 54029376p-Nitrobenzyl 2-diazo-3-trimethylsilyloxy-3-butenoate収率 98.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile
溶媒

反応条件

温度
40 °C

実験手順

Into 5 ml of dry acetonitrile were suspended 263 mg (1 millimole) of p-nitrobenzyl 2-diazoacetoacetate and 122 mg (1.4 millimoles) of lithium bromide. To the mixture were added 220 μl (1.6 millimoles) of triethylamine and then 190 μl (1.5 millimoles) of trimethylsilyl chloride while agitating under an argon atmosphere at a room temperature. The resultant was heated up to 40° C. and agitated at the same temperature overnight, followed by concentration under a reduced pressure. To the residue was added 20 ml of dry hexane, and the resultant was agitated for 30 min. at a room temperature. Insoluble materials were removed by filtration and the filtrate was concentrated to dryness under a reduced pressure to give 330 mg (yield 87%) of the desired compound in a yellow solid. The physical properties of the product were in agreement with those of the product obtained in Example 1.

後処理

  1. concentrationfollowed by concentration under a reduced pressure
  2. additionTo the residue was added 20 ml of dry hexane
  3. stirringthe resultant was agitated for 30 min. at a room temperature
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated to dryness under a reduced pressure

出典と根拠

ORDレコード
ord-7c2b49358fa04611bec0fd72f531689c
出典データセット
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05071966

反応ノート

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