Acetaldehyde → 5-(2-Hydroxypropan-1-yl)-2-phenyl-1,3-dioxane

HRID 728485ノート

反応式

HRID 728485 の反応式
Br[CH2:2][CH:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][CH2:4]1.[Mg].[CH:16](=[O:18])[CH3:17].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[OH:18][CH:16]([CH3:17])[CH2:2][CH:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][CH2:4]1

参加物

7

反応物 4

HCID 177AcetaldehydeHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 148351015-Bromomethyl-2-phenyl-1,3-dioxane

生成物 1

HCID 198842565-(2-Hydroxypropan-1-yl)-2-phenyl-1,3-dioxane

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-70 °C

実験手順

To a solution of 19.39 g (75.4 mM) of 5-bromomethyl-2-phenyl-1,3-dioxane m2 in 200 ml of tetrahydrofuran is added 1.923 g (79.17 mM) of magnesium and the mixture is allowed to react for 7 hours under ultrasonic bibration. The mixture is cooled to -70° C. and 21.27 ml (377 mM) of acetaldehyde is added and then the mixture is stirred at 0° C. for 15 hours. The mixture is poured into an ice-cooled saturated aqueous ammonium chloride solution and the product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated. By eliminating the polar impurity by passing short column of silica gel, 11.353 g of the crude titled compound m3 is obtained which is used to the next reaction without further purification.

後処理

  1. customto react for 7 hours under ultrasonic bibration
  2. washThe ethyl acetate layer is washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

出典と根拠

ORDレコード
ord-c843df144656408986309cb6590631f3
出典データセット
uspto-grants-1991_09
特許番号
US05047540

反応ノート

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