Allyltributylstannane → 3-Allyl-4-methyl-benzoic acid methyl ester

HRID 1991016ノート

反応式

HRID 1991016 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15].[Cl-].[Li+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][C:11]([CH3:12])=[C:2]([CH2:15][CH:14]=[CH2:13])[CH:3]=1

参加物

6

反応物 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 7015747Methyl 3-bromo-4-methylbenzoate

生成物 1

HCID 591286443-Allyl-4-methyl-benzoic acid methyl ester収率 101.8%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
95 °C

実験手順

Argon was bubbled into a solution of methyl 3-bromo-4-methylbenzoate (11.45 g, 50 mmol), allyltributyl-stannane (16.72 g, 50.5 mmol) and lithium chloride (5.30 g, 125 mmol) in DMF (100 mL) with magnetic stirring for 20 minutes. Dichlorobis(triphenyl-phosphine)palladium (0.81 g, 1.16 mmol) was then added and mixture heated at 95° C. for 1.5 hours. After cooling to room temperature, the mixture was partitioned between ether-hexanes (1:1 V/V) and water. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Isco RediSep 330 g silica gel, 5% then 35% dichloromethane in hexanes) to give 3-allyl-4-methyl-benzoic acid methyl ester (9.68 g, 100%) as a colorless oil.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between ether-hexanes (1:1 V/V) and water
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (Isco RediSep 330 g silica gel, 5%

出典と根拠

ORDレコード
ord-1a01e4bda73d4eecab1e40d3e29a28bc
出典データセット
uspto-grants-2010_01
特許番号
US07645764B2

反応ノート

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