Toluene → 3-(1-Tritylimidazol-4-YL) propionaldehyde

HRID 76878

반응식

HRID 76878 반응식
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1.C1(C)C=CC=CC=1.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl.CO>[C:11]([N:9]1[CH:10]=[C:6]([CH2:5][CH2:4][CH:3]=[O:2])[N:7]=[CH:8]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

7

반응물 4

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 10475868Methyl 3-(1-Tritylimidazol-4-yl) Propionate

생성물 1

HCID 114514283-(1-Tritylimidazol-4-YL) propionaldehyde

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

3-(1-Trityl-1H-imidazol-4-yl)propionic acid methyl ester (7.75 g, 19.5 mmol), J. Org. Chem. 2000, 65, 2229-2230, is dissolved in DCM (300 mL) and cooled to −78° C. To this is added a toluene solution of DIBAL (21.0 mL, 1.5 M). After 2 h MeOH (20 mL) is added followed by saturated aqueous Rochelle salt solution (50 mL). The mixture is partitioned between DCM and saturated aqueous Rochelle salt solution. The organic phase is dried (Na2SO4) and evaporated. The crude residue is purified via flash column chromatography (MeOH/DCM 1:99→MeOH/DCM 5:95) to give the aldehyde, 3-(1-trityl-1H-imidazol-4-yl)propionaldehyde as a yellow gum (cas #184030-88-4). 1H NMR (CDCl3) δ 9.83 (s, 1H), 7.38-7.31 (m, 10H), 7.16-7.12 (m, 6H), 6.58 (s, 1H), 2.90 (t, J=8.0 Hz, 2H), 2.83-2.79 (m, 2H).

후처리

  1. customThe mixture is partitioned between DCM and saturated aqueous Rochelle salt solution
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. customevaporated
  4. customThe crude residue is purified via flash column chromatography (MeOH/DCM 1:99→MeOH/DCM 5:95)

출처 및 근거

ORD 기록
ord-be1999ba89174bc396a9555d08f6c297
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835646B2

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