2-Dimethylaminopyridine → (Trimethylsilyl)ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate

HRID 610341

반응식

HRID 610341 반응식
[CH3:1][C:2]1([CH3:24])[C:11]2[CH:10]=[C:9]([C:12]#[C:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)[CH:8]=[CH:7][C:6]=2[C:5](=[O:23])[CH2:4][CH2:3]1.CN(C1C=CC=CN=1)C.[CH3:34][Si:35]([CH:38](O)[CH3:39])([CH3:37])[CH3:36].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH3:1][C:2]1([CH3:24])[C:11]2[CH:10]=[C:9]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([O:20][CH2:39][CH2:38][Si:35]([CH3:37])([CH3:36])[CH3:34])=[O:19])=[CH:21][CH:22]=3)[CH:8]=[CH:7][C:6]=2[C:5](=[O:23])[CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 124478981-(Trimethylsilyl)ethanolHCID 153455474-((5,6,7,8-Tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoic acid2회

생성물 1

HCID 54412444(Trimethylsilyl)ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

To a solution of 0.24 g (0.73 mmol) of 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoic acid (Compound 7) in 10 ml of dry CH2Cl2 was added 0.09 g (0.74 mmol) of dimethylaminopyridine, 0.115 ml (0.80 mmol) of trimethylsilylethanol and 0.17 g (0.88 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride. The reaction mixture was stirred at 25° C. for 5 hours, washed with sat. aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to an oil. Purification by flash chromatography (silica, 10% EtOAc-hexane) yielded the title compound as a white solid.

후처리

  1. washwashed with sat. aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo to an oil
  4. customPurification by flash chromatography (silica, 10% EtOAc-hexane)

출처 및 근거

ORD 기록
ord-008a65ebb3b247e395061222e322bef9
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998471

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