Triacetoxyperiodinane → HCID 86705754, 화합물

HRID 1054551노트

반응식

HRID 1054551 반응식
[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]2[N:6]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[N:8][C:4]=2[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]2[N:6]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:7]([CH2:9][CH2:10][CH2:11][CH:12]=[O:13])=[N:8][C:4]=2[CH:3]=1

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 67814888HCID 67814888, 화합물

생성물 1

HCID 86705754HCID 86705754, 화합물수율 59.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-(5,6-Dichloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)butan-1-ol (1.008 g, 2.59 mmol) was dissolved in DCM (35 ml) and Dess-Martin reagent (1.208 g, 2.85 mmol) was added at r.t. under N2. The reaction was left for 2 hrs. The reaction was quenched by the addition of 1M Na2S2O3 solution (10 ml), sat. NaHCO3 solution (40 ml) and DCM (80 ml). The organic layer was separated and the aqueous layer was extracted with DCM (3×80 ml). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give the crude product. The product was purified by silica flash column chromatography using between 15% EtOAc:85% heptanes and 100% EtOAc as eluent to give the product as a pale yellow oil (0.595 g, 59%): MS (ESI+) for C17H24Cl2N2O2Si m/z 388.4 [M+H]+; LC purity 91% (ret. time, 1.74 min); 1H NMR (500 MHz, CDCl3) δ 9.82 (s, 1H), 7.79 (s, 1H), 7.53 (s, 1H), 5.44 (s, 2H), 3.43-3.67 (m, 2H), 2.97 (t, J=7.49 Hz, 2H), 2.69 (t, J=7.25 Hz, 2H), 2.23 (quin, J=7.13 Hz, 2H), 0.78-1.02 (m, 2H), −0.02 (s, 9H).

후처리

  1. customThe reaction was quenched by the addition of 1M Na2S2O3 solution (10 ml), sat. NaHCO3 solution (40 ml) and DCM (80 ml)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (3×80 ml)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product
  8. customThe product was purified by silica flash column chromatography

출처 및 근거

ORD 기록
ord-d21da1badb6f407db3124ed32f245350
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394310B2

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