1,2-Dimethoxyethane → 4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-2-vinyl-pyridine

HRID 1959603노트

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HRID 1959603 반응식
Cl[C:2]1[C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[C:6]([CH3:16])[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].CO[CH2:25][CH2:26]OC>O.[Pd]>[CH3:16][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH:25]=[CH2:26])[C:7]=1[CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1

참가 물질

6

반응물 3

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 441909462-Chloro-4-methyl-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine

생성물 1

HCID 441905854-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-2-vinyl-pyridine

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 962Water용매

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온도
100 °C

실험 절차

2-Chloro-4-methyl-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine (500 mg. 2.07 mmol) was dissolved in a mixture of 1,2-dimethoxyethane (16.5 mL) and water (7 mL). K2CO3 (286 mg. 2.07 mmol) and 2,4,6-trivinyl-cyclotriboroxane pyridine complex (498 mg. 2.07 mmol) were added and the reaction mixture was degassed two times before the addition of Pd((PPh3)4 (120 mg. 0.10 mmol). The reaction mixture was stirred at 100° C. for 18 h. The solvents were removed in vacuo and the residue was purified by flash chromatography on silica gel (elution with hexane/EtOAc 6:1) to give the title compound. MS (m/z): 234.1 [M+H+]

후처리

  1. customthe reaction mixture was degassed two times
  2. customThe solvents were removed in vacuo
  3. customthe residue was purified by flash chromatography on silica gel (elution with hexane/EtOAc 6:1)

출처 및 근거

ORD 기록
ord-ecf74380dd4e4471a5c7693d02b4cff4
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410134B2

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