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

HRID 1959603ノート

反応式

HRID 1959603 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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+]

後処理

  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)

出典と根拠

ORDレコード
ord-ecf74380dd4e4471a5c7693d02b4cff4
出典データセット
uspto-grants-2013_04
特許番号
US08410134B2

反応ノート

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