Diisobutylaluminumhydride → HCID 59682036, 화합물

HRID 1394653노트

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HRID 1394653 반응식
[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]

참가 물질

4

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 59682038HCID 59682038, 화합물

생성물 1

HCID 59682036HCID 59682036, 화합물수율 38%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-f0fab459e995413c8d3f8a628a227e25
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348359B2

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