HCID 13827091、化合物 → HCID 504663、化合物

HRID 978358ノート

反応式

HRID 978358 の反応式
[CH3:1][Li].[CH2:3]([O:5][C:6]1[O:11][C:10](=[O:12])[C:9]2[C:13]([CH2:17]Br)=[CH:14][CH:15]=[CH:16][C:8]=2[N:7]=1)[CH3:4]>CCOCC.O1CCCC1>[CH2:3]([O:5][C:6]1[O:11][C:10](=[O:12])[C:9]2[C:13]([CH2:17][CH3:1])=[CH:14][CH:15]=[CH:16][C:8]=2[N:7]=1)[CH3:4]

参加物

5

反応物 2

HCID 13827091HCID 13827091、化合物HCID 178418348HCID 178418348、化合物

生成物 1

HCID 504663HCID 504663、化合物

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-25 °C

実験手順

Methyl lithium (4.69 ml, 1.4M, Aldrich) was added to a suspension of cuprous iodide (0.62 gm) in anhydrous ether under argon at -78° C. The solution was stirred at -25° C. for 25 min. This solution was added to a solution of 2-ethoxy-5-bromomethyl-4H-3,1-benzoxazin-4-one (200 mg) in 15 ml anhydrous ether and 3 ml dry tetrahydrofuran at -60° C. Reaction was monitored by TLC until reaction completion. The reaction was quenched with saturated ammonium chloride solution and filtered. The filtrate was extracted in the usual manner. The ethereal layer was washed with water, dried over magnesium sulphate and evaporated to give an oil. The material was purified by thick layer chromatography (Rf =0.75, 3-% ethyl acetate: petroleum ether), to give 2-ethoxy-5-ethyl-4H-3,1-benzoxazin-4-one, m.p. 89°-91° C., H NMR: 1.3, 1.5 (2t, 6H, 2CH3), 3.2 (q, 2H, CH2), 4.5 (q, 2H, OCH2CH3), 7.2 (m, 2H, ArH), 7.6 (t, 1H, ArH).

後処理

  1. customReaction
  2. customwas monitored by TLC until reaction completion
  3. customThe reaction was quenched with saturated ammonium chloride solution
  4. filtrationfiltered
  5. extractionThe filtrate was extracted in the usual manner
  6. washThe ethereal layer was washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customto give an oil
  10. customThe material was purified by thick layer chromatography (Rf =0.75, 3-% ethyl acetate: petroleum ether)

出典と根拠

ORDレコード
ord-229cdcf9dcae47bb907b54dde74fdee0
出典データセット
uspto-grants-1987_05
特許番号
US04665070

反応ノート

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