Sodium Bicarbonate → 5-(3-Bromobenzyl)-2,2-dimethyl-1,3-dioxane

HRID 1796364ノート

反応式

HRID 1796364 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][CH:6]([CH2:9][OH:10])[CH2:7][OH:8].O.[C:15]1(C)[CH:20]=CC(S(O)(=O)=O)=C[CH:16]=1.C(=O)([O-])O.[Na+]>CC(C)=O.C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][CH:6]1[CH2:7][O:8][C:15]([CH3:20])([CH3:16])[O:10][CH2:9]1

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 218669482-(3-Bromobenzyl)-1,3-propanediol

生成物 1

HCID 218667465-(3-Bromobenzyl)-2,2-dimethyl-1,3-dioxane収率 1,400.7%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 241Benzene溶媒

実験手順

2-(3-Bromobenzyl)-1,3-propanediol (1.85 g) was dissolved in a mixture of 8 ml of acetone/18 ml of benzene, and 70 mg of p-toluenesulfonic acid monohydrate was added. The solution was subjected to azeotropic dehydration with Dean-Stark apparatus for 1 hour. After addition of saturated sodium hydrogen carbonate solution, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=4:1) to provide 1.47 g of the objective compound as colorless oil.

後処理

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-4d8bfd9646dc49359630e09d0eade922
出典データセット
uspto-grants-2006_04
特許番号
US07030143B2

反応ノート

読み込み中…