Hydrochloric Acid → (Z)-9-(Triisopropylsilyloxy)-8,9-dihydro-7H-cyclohepta[b]pyridine

HRID 1666132노트

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HRID 1666132 반응식
Cl.[CH:2]([Si:5]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[O:6][CH:7]([C:12]1[C:17]([CH:18]=[CH2:19])=[CH:16][CH:15]=[CH:14][N:13]=1)[CH2:8][CH2:9]C=C)([CH3:4])[CH3:3].N#N>C(Cl)Cl>[CH:20]([Si:5]([CH:23]([CH3:25])[CH3:24])([CH:2]([CH3:4])[CH3:3])[O:6][CH:7]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:17]2[CH:18]=[CH:19][CH2:9][CH2:8]1)([CH3:22])[CH3:21]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 579114762-(1-(Triisopropylsilyloxy)pent-4-enyl)-3-vinylpyridine

생성물 1

HCID 57911494(Z)-9-(Triisopropylsilyloxy)-8,9-dihydro-7H-cyclohepta[b]pyridine수율 70.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
40 °C

실험 절차

Hydrogen chloride (5.64 mL, 11.28 mmol)(10 mL, 2M diethyl ether solution) was added to the CH2Cl2 (25 mL) solution of 2-(1-(triisopropylsilyloxy)pent-4-enyl)-3-vinylpyridine (3.9 g, 11.28 mmol). The solvent was removed via vacuum and the corresponding HCl salt was azeotroped by benzene twice. The reaction was charged with CH2Cl2 (500 mL) and purged with N2 for 10 min before addition of Grubb II (0.192 g, 0.226 mmol). The reaction was heat to 40° C. for 3 hours, LCMS showed no starting material left. The reaction was washed with saturated NaHCO3 solution once. The CH2Cl2 was separated, dried (Na2SO4), filtered and concentrated. Flash column by ether in hexane from 0 to 25% gave the desired product as yellow oil (2.54 g, 71%yield). MS(ESI)[M+H+]=318.35.

후처리

  1. customThe solvent was removed via vacuum
  2. customthe corresponding HCl salt was azeotroped by benzene twice
  3. additionThe reaction was charged with CH2Cl2 (500 mL)
  4. waitleft
  5. washThe reaction was washed with saturated NaHCO3 solution once
  6. customThe CH2Cl2 was separated
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a18251fe0c464a55b3365e23974c5117
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044043B2

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