Diisobutylaluminumhydride → HCID 59682036、化合物

HRID 1394653ノート

反応式

HRID 1394653 の反応式
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([C:24]3[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[CH:27]=[C:26]([CH:33]([CH3:35])[CH3:34])[C:25]=3[O:36][CH2:37][CH3:38])=[CH:22][N:23]=2)[CH:20]=1)=O>ClCCl>[CH2:37]([O:36][C:25]1[C:26]([CH:33]([CH3:34])[CH3:35])=[CH:27][C:28]([CH:30]([CH3:32])[CH3:31])=[CH:29][C:24]=1[C:21]1[N:19]2[CH:20]=[C:15]([CH2:13][OH:12])[CH:16]=[CH:17][C:18]2=[N:23][CH:22]=1)[CH3:38]

参加物

4

反応物 2

HCID 21225700DiisobutylaluminumhydrideHCID 59682038HCID 59682038、化合物

生成物 1

HCID 59682036HCID 59682036、化合物収率 38%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

Diisobutylaluminum hydride (2.4 ml, 1M soln., 2.4 mmol) was added dropwise to a solution of 3-(2-ethoxy-3,5-diisopropyl-phenyl)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (300 mg, 0.79 mmol) in dichloromethane (10 mL) which had been cooled to −78° C. under a nitrogen atmosphere. After the addition was complete, the reaction was kept at −78° C. for 4 h, then quenched with with methanol (10 mL). After addition of the methanol, the mixture was poured into water, filtered and the solution evaporated to a residue. The residue was purified by silica gel chromatography (2.5% MeOH in dichloromethane) to give [3-(2-ethoxy-3,5-diisopropyl-phenyl)-imidazo[1,2-a]pyridin-6-yl]-methanol as a clear glass (102 mg, 38%). 1H NMR (250 MHz, CDCl3): δ 8.01 (s, 1H), 7.70 (bs, 1H), 7.64 (d, 1H, J=9.4), 7.24 (m, 2H), 7.12 (d, 1H, J=0.62), 4.73 (s, 1H), 3.45 (m, 1H), 3.35 (q, 2H, J=7.0), 1.34 (s, 3H), 1.31 (s, 3H), 1.30 (s, 3H), 1.29 (s, 3H), 0.84 (t, 3H, J=7.0), MS [EI+] 353 (M+H)+.

後処理

  1. additionAfter the addition
  2. customquenched with with methanol (10 mL)
  3. additionAfter addition of the methanol
  4. additionthe mixture was poured into water
  5. filtrationfiltered
  6. customthe solution evaporated to a residue
  7. customThe residue was purified by silica gel chromatography (2.5% MeOH in dichloromethane)

出典と根拠

ORDレコード
ord-f0fab459e995413c8d3f8a628a227e25
出典データセット
uspto-grants-2008_03
特許番号
US07348359B2

反応ノート

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