Diisobutylaluminum hydride → 4-(Benzoxazol-2-yl)benzyl alcohol

HRID 8975

反応式

HRID 8975 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[CH:12][CH:11]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:19]=[CH:18][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 650931Methyl 4-(benzoxazol-2-yl)benzoate

生成物 1

HCID 153890174-(Benzoxazol-2-yl)benzyl alcohol収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 4-(benzoxazol-2-yl)-benzoate (0.20 g, 0.8 mmol) in THF (8 mL) at −78° C. was added a solution of DIBAL-H (4.0 mL, 1.0 M in THF, 4.0 mmol). The reaction was allowed to warm to room temperature, stirred for 1 h and quenched with a saturated potassium sodium tartrate solution (15 mL). The biphasic mixture was stirred vigorously for 1 h, the phases separated and the organic layer dried (MgSO4), filtered and concentrated to give the title alcohol (0.16 g, 89%). 1H NMR (CDCl3) δ 1.80 (t, 1H (Oh)), 4.82 (d, 2H, J=6.0 Hz), 7.36 (m, 2H), 7.55 (d, 2H, J=8.4 Hz), 7.60 (m, 1H), 7.78 (m, 1H), 8.26 (d, 2H, J=8.4 Hz).

後処理

  1. customquenched with a saturated potassium sodium tartrate solution (15 mL)
  2. stirringThe biphasic mixture was stirred vigorously for 1 h
  3. customthe phases separated
  4. dry with materialthe organic layer dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-0439c2fefc7c49b5a81e78ca699c8b1a
出典データセット
uspto-grants-2006_08
特許番号
US07091217B2

関連ノート

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