Hydrochloric Acid → HCID 22221337、化合物

HRID 1794400ノート

反応式

HRID 1794400 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[CH:9][C:8]=2[CH2:12][CH2:13][C:14](OC)=[O:15])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[CH:9][C:8]=2[CH2:12][CH2:13][CH2:14][OH:15])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221223HCID 22221223、化合物

生成物 1

HCID 22221337HCID 22221337、化合物収率 73%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 3-[5-(5-chloro-2-thienyl)-4-isoxazolyl]propionate (3.10 g) in tetrahydrofuran (80 ml) was gently added diisobutylaluminum hydride (1.5 M toluene solution, 17 ml) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and 3-[5-(5-chloro-2-thienyl)-4-isoxazolyl]propan-1-ol (2.02 g, yield 73%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). NMR (CDCl3) δ: 1.41 (1H, br t, J=5 Hz), 1.8–2.0 (2H, m), 2.73 (2H, t, J=8 Hz), 3.73 (2H, td, J=6, 5 Hz), 6.98 (1H, d, J=4 Hz), 7.29 (1H, d, J=4 Hz), 8.17 (1H, s).

後処理

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-32f55f8600c84fa9930be7c3407060f0
出典データセット
uspto-grants-2006_04
特許番号
US07022725B2

反応ノート

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