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Hydrochloric Acid → 3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazole-5-carbaldehyde

HRID 1245393
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HRID 1245393 반응식
C[O:2][CH:3](OC)[CH:4]1[O:8][N:7]=[C:6]([C:9]2[CH:27]=[CH:26][C:12]([O:13][CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=[C:17]([CH3:25])[CH:16]=3)=[CH:11][CH:10]=2)[CH2:5]1.Cl>C1COCC1>[CH3:25][C:17]1[CH:16]=[C:15]([CH2:14][O:13][C:12]2[CH:26]=[CH:27][C:9]([C:6]3[CH2:5][CH:4]([CH:3]=[O:2])[O:8][N:7]=3)=[CH:10][CH:11]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 219111774-[4-(5-Dimethoxymethyl-4,5-dihydro-isoxazol-3-yl)-phenoxymethyl]-2-methyl-quinoline

생성물 1

HCID 218980783-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazole-5-carbaldehyde수율 72%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The product from step 10a (0.4 g, 1.0 mmol) was dissolved in THF (5 mL) and 6 N HCl (5 mL) and heated to 60° C. for 2.5 h. The reaction was cooled and concentrated, and the aqueous layer was neutralized with NaOH and then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The oil was purified with FCC eluting ethyl acetate:methylene chloride (80:20) to give 3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazole-5-carbaldehyde (0.1 g, 72%) as an oil. MS found: (M+H)+=347.

후처리

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe oil was purified with FCC
  9. washeluting ethyl acetate:methylene chloride (80:20)

출처 및 근거

ORD 기록
ord-46d410f93ad44a7c80801e13609bacd7
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07125870B2

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