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

HRID 1245393
ノート
印刷プレビュー

反応式

HRID 1245393 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-46d410f93ad44a7c80801e13609bacd7
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07125870B2

反応ノート

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