Dopac → 5-(2-Hydroxyethyl)-2-methyl-1,3-benzodioxole

HRID 2259752

反応式

HRID 2259752 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[OH:8].[C:13](OC=C)(=O)[CH3:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O1CCCC1.[Hg]=O.O>[OH:12][CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][C:7]2[O:8][CH:13]([CH3:14])[O:1][C:2]=2[CH:3]=1

参加物

10

反応物 4

HCID 547DopacHCID 7904Vinyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 190016255-(2-Hydroxyethyl)-2-methyl-1,3-benzodioxole収率 74.6%

試薬・触媒・溶媒 5

HCID 30856Mercuric oxide触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A suspension of 1.0 g of 3,4-dihydroxyphenylacetic acid, 1.4 g of vinyl acetate, 6 mg of mercury oxide (yellow) and 0.03 ml of boron fluoride/ethyl etherate in 9 ml of toluene was stirred at room temperature for 14 h. The reaction mixture was diluted with ethyl acetate and washed with water and an aqueous common salt solution. The organic layer was dried over magnesium sulfate and the solvent was distilled off. An oil thus obtained was dissolved in 10 ml of tetrahydrofuran and the solution was added dropwise to a suspension of 0.5 g of lithium aluminum hydride in tetrahydrofuran under cooling with ice. The mixture was stirred at room temperature for 1 h. 0.5 ml of water, then 0.5 ml of a 15% aqueous sodium hydroxide solution and finally 1.5 ml of water were added thereto and an insoluble matter was filtered off. The filtrate was concentrated and treated according to silica gel column chromatography (ethyl acetate/hexane=1:1) to obtain 0.8 g of the intended compound in the form of a colorless oil.

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customAn oil thus obtained
  5. temperatureunder cooling with ice
  6. stirringThe mixture was stirred at room temperature for 1 h
  7. filtrationan insoluble matter was filtered off
  8. concentrationThe filtrate was concentrated
  9. additiontreated

出典と根拠

ORDレコード
ord-237408a16d374957be2a2740e478e8d8
出典データセット
uspto-grants-1995_12
特許番号
US05475024

関連ノート

読み込み中…