HCID 13827091, 화합물 → HCID 504663, 화합물

HRID 978358노트

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HRID 978358 반응식
[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]

참가 물질

5

반응물 2

HCID 13827091HCID 13827091, 화합물HCID 178418348HCID 178418348, 화합물

생성물 1

HCID 504663HCID 504663, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
-25 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-229cdcf9dcae47bb907b54dde74fdee0
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04665070

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