Potassium Carbonate → 4-Methoxy-5-methyl-2-vinyl-pyridine

HRID 1908812ノート

反応式

HRID 1908812 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[CH:4][N:3]=1.B1(C=C)OB([CH:17]=[CH2:18])OB(C=C)O1.C1C=CN=CC=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][O:8][C:6]1[C:5]([CH3:10])=[CH:4][N:3]=[C:2]([CH:17]=[CH2:18])[CH:7]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 790022772-Chloro-4-methoxy-5-methylpyridine

生成物 1

HCID 670271894-Methoxy-5-methyl-2-vinyl-pyridine収率 62.9%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-chloro-4-methoxy-5-methyl-pyridine (2.91 g, 18.5 mmol) in DME (75 mL), 2,4,6-trivinylcyclotriboroxane pyridine complex (3.13 g, 13.0 mmol) followed by 2 M aq. K2CO3 solution (25 mL) is added. The mixture is degassed and put under argon before Pd(PPh3)4 (384 mg, 0.332 mmol) is added. The mixture is stirred at 80° C. for 15 h before it is cooled to rt, diluted with water and extracted with diethyl ether. The org. extract is washed with sat. aq. NaHCO3 solution, dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 4-methoxy-5-methyl-2-vinyl-pyridine (1.22 g) as a white solid; LC-MS: tR=0.52 min, [M+1]+=150.08.

後処理

  1. additionis added
  2. customThe mixture is degassed
  3. additionis added
  4. temperatureis cooled to rt
  5. extractionextracted with diethyl ether
  6. extractionextract
  7. washis washed with sat. aq. NaHCO3 solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

出典と根拠

ORDレコード
ord-ca2ada2e64134ac2912c9f7c0ff006f3
出典データセット
uspto-grants-2013_12
特許番号
US08598208B2

反応ノート

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