Sodium Azide → Ethyl 3-azido-2-hydroxypropanoate

HRID 1453836ノート

反応式

HRID 1453836 の反応式
Br[CH2:2][CH:3]([OH:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N-:10]=[N+:11]=[N-:12].[Na+]>CCO.O>[N:10]([CH2:2][CH:3]([OH:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N+:11]=[N-:12]

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 13180684Ethyl 3-bromo-2-hydroxypropanoate

生成物 1

HCID 10888191Ethyl 3-azido-2-hydroxypropanoate

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

反応条件

温度
90 °C

実験手順

To a solution of ethyl 3-bromo-2-hydroxypropanoate (22.1 g, 112.0 mmol) in EtOH/H2O (1:1) was added sodium azide (10.9 g, 168.0 mmol). The reaction was stirred and heated to 90° C. for 3 days. The EtOH was removed in vacuo and the remaining aqueous solution was extracted with CHCl3 several times. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to afford the azide as an orange oil. 1H NMR (400 MHz, d6-DMSO) δ 5.96 (d, J=5.6 Hz, 1H), 4.31-4.28 (m, 1H), 4.19-4.08 (m, 2H), 3.51-3.40 (m, 2H), 1.28-1.17 (m, 3H).

後処理

  1. customThe EtOH was removed in vacuo
  2. extractionthe remaining aqueous solution was extracted with CHCl3 several times
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b2e2702fe4a14ab487c9f275c9e007fd
出典データセット
uspto-grants-2009_01
特許番号
US07476666B2

反応ノート

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