Toluene → HCID 20187900、化合物

HRID 2308826ノート

反応式

HRID 2308826 の反応式
[Na].[CH3:2][C:3]([OH:9])([CH3:8])[CH:4]([OH:7])[CH2:5][OH:6].[C:10]1([CH3:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[CH2:16]([O:6][CH2:5][CH:4]([O:7][CH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([CH3:8])([OH:9])[CH3:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:16]([O:6][CH2:5][CH:4]([OH:7])[C:3]([CH3:8])([OH:9])[CH3:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 1140Toluene2 回HCID 5360545SodiumHCID 130445963-Methyl-1,2,3-butanetriol

生成物 2

HCID 20187900HCID 20187900、化合物HCID 20187911HCID 20187911、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 0.460 g of sodium in 10 ml of ethanol is treated with 2.4 g of (RS)-3-methyl-1,2,3-butanetriol. 20 ml of toluene are added thereto and, with the simultaneous dropwise addition of 60 ml of toluene, solvent is distilled off slowly until the distillate amounts to 75 ml. The residual suspension is suction filtered, the residue is washed with ether and dried at room temperature/11 Torr. The salt is suspended in 10 ml of tetrahydrofuran, then 0.740 g of tetrabutylammonium iodide and 4.0 ml of benzyl bromide are added and the mixture is stirred at room temperature for 3 days. The mixture is diluted with benzene and concentrated at 30°/11 Torr. The residue is chromatographed on 30 g of silica gel with hexane/ether (4:1). There are thus obtained, besides 0.616 g of (RS)-1,2-dibenzyloxy-3-methyl-3-butanol, as the polar fraction 1.15 g of the desired product as a colourless oil of boiling point 150°/2 Torr (bulb-tube).

後処理

  1. distillationis distilled off slowly until the distillate amounts to 75 ml
  2. filtrationsuction filtered
  3. washthe residue is washed with ether
  4. customdried at room temperature/11 Torr
  5. addition0.740 g of tetrabutylammonium iodide and 4.0 ml of benzyl bromide are added
  6. additionThe mixture is diluted with benzene
  7. concentrationconcentrated at 30°/11 Torr
  8. customThe residue is chromatographed on 30 g of silica gel with hexane/ether (4:1)

出典と根拠

ORDレコード
ord-259d634c2bd14586bf41bbee12762488
出典データセット
uspto-grants-1987_09
特許番号
US04691032

反応ノート

読み込み中…