Potassium Carbonate → Tert-butyl (1-phenylbut-3-yn-1-yl)carbamate

HRID 659131

反応式

HRID 659131 の反応式
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][CH:10]=O)([CH3:4])([CH3:3])[CH3:2].[N+](=[C:21](P(=O)(OC)OC)C(=O)C)=[N-].C(=O)([O-])[O-].[K+].[K+]>CO>[C:12]1([CH:8]([NH:7][C:6](=[O:18])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:9][C:10]#[CH:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 15087934Tert-butyl N-(3-oxo-1-phenylpropyl)carbamate2 回HCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one2 回

生成物 1

HCID 57429813Tert-butyl (1-phenylbut-3-yn-1-yl)carbamate収率 87.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To the solution of 1.2 g of tert-butyl 3-oxo-1-phenylpropylcarbamate (Formula 12) and 1.38 g of dimethyl 1-diazo-2-oxopropylphosphonate (Formula 15) in 60 mL of methanol at 0° C. was added 1.32 g of potassium carbonate. The mixture was stirred at room temperature for 16 hours then quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. Column chromatography (5% ethyl acetate/hexane) gave 1.03 g (87%) of tert-butyl 1-phenylbut-3-ynylcarbamate (Formula 16) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.43 (s, 9H), 1.98-2.00 (m, 1H), 2.6-2.8 (m, 2H), 4.88 (br, 1H), 5.16 (br, 1H), 7.23-7.37 (m, 5H).

後処理

  1. customthen quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6e95369fee4741a88a46b9b467e411f2
出典データセット
uspto-grants-2011_12
特許番号
US08080570B2

関連ノート

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