Ethylene Glycol → 2-(3-Bromophenyl)-2-methyl-1,3-dioxolane

HRID 42757

反応式

HRID 42757 の反応式
N#N.[Br:3][C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1.[CH2:13](O)[CH2:14][OH:15].COC(OC)OC.C([O-])([O-])=O.[Na+].[Na+]>>[Br:3][C:4]1[CH:5]=[C:6]([C:10]2([CH3:11])[O:15][CH2:14][CH2:13][O:12]2)[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 5

HCID 174Ethylene GlycolHCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 165023'-Bromoacetophenone

生成物 1

HCID 109992182-(3-Bromophenyl)-2-methyl-1,3-dioxolane

反応条件

温度
95 °C

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(3-bromo-phenyl)-ethanone (1360 mg, 6.83 mmol) in ethylene glycol (8.00 mL, 143.46 mmol) was treated with trimethylorthoformate (1.50 mL, 13.68 mmol) followed by LiBF4 (131 mg, 1.37 mmol). The reaction mixture was heated at 95° C. for 15 h. Sat. aq. Na2CO3 was added and the mixture was extracted twice with ether and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 hept-EA) gave the title compound as a pale yellow oil: TLC:rf (10:1 hept-EA)=0.34. LC-MS-conditions 02: tR=1.01 min.

後処理

  1. extractionthe mixture was extracted twice with ether
  2. dry with materialthe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customPurification of the residue by FC (20:1 hept-EA)

出典と根拠

ORDレコード
ord-2395729cc9094f8db19164bab0b1ef65
出典データセット
uspto-grants-2013_09
特許番号
US08536209B2

関連ノート

読み込み中…