Methyl 3-(1-Tritylimidazol-4-yl) Propionate → 3-(1-Tritylimidazol-4-YL) propionaldehyde

HRID 22562

반응식

HRID 22562 반응식
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([N:30]1[CH:34]=[C:33]([CH2:35][CH2:36][C:37](OC)=[O:38])[N:32]=[CH:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.C(Cl)Cl>[C:11]([N:30]1[CH:34]=[C:33]([CH2:35][CH2:36][CH:37]=[O:38])[N:32]=[CH:31]1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 2

HCID 10475868Methyl 3-(1-Tritylimidazol-4-yl) PropionateHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 114514283-(1-Tritylimidazol-4-YL) propionaldehyde수율 50.8%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

A solution of 44.4 mmole of diisobutylaluminium hydride in 29 ml of toluene is added to a solution of 8.79 g of methyl 3-(1-tritylimidazol-4-yl)propionate in 175 ml of methylene chloride at -72° under nitrogen. After 5 min the reaction is quenched by adding 14 ml of methanol followed by 90 ml of water. The reaction mixture is allowed to warm to room temperature and is filtered through celite. The organic phase is separated, dried over sodium sulfate and evaporated to a yellow oil which is chromatographed on 280 g of silica with ether to yield 4.13 g of 3-(1-tritylimidazol-4-yl)propionaldehyde as an oil. IR (CDCl3): 2830, 2740, 1730 cm-1.

후처리

  1. customAfter 5 min the reaction is quenched
  2. additionby adding 14 ml of methanol
  3. filtrationis filtered through celite
  4. customThe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated to a yellow oil which
  7. customis chromatographed on 280 g of silica with ether

출처 및 근거

ORD 기록
ord-049338e45954404f8f1560be569823c7
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428160

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