Sodium Hydroxide → (2S)-(+)-(5-chloro-2-cyanophenoxy)-2,3-epoxypropane

HRID 654073ノート

反応式

HRID 654073 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[N:10])=[C:6]([OH:8])[CH:7]=1.[CH2:11]1[O:13][C@H:12]1[CH2:14]Cl.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[N:10])=[C:6]([CH:7]=1)[O:8][CH2:14][C@H:12]1[O:13][CH2:11]1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 2734062(-)-EpichlorohydrinHCID 34427894-Chloro-2-hydroxybenzonitrile

生成物 1

HCID 10774787(2S)-(+)-(5-chloro-2-cyanophenoxy)-2,3-epoxypropane収率 35.2%

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 1140Toluene溶媒

実験手順

A mixed solution of 5.0 g of 5-chloro-2-cyano-phenol and 6.0 g of R-(-)-epichlorohydrin was heated at 120° C. for 2 hours under a nitrogen stream. Toluene (50 ml), 0.1 g of benzyl triethylammonium chloride and 20 ml of a 30% sodium hydroxide were added, and the mixture was stirred at room temperature for 2 hours. The organic layer was separated and dried over magnesium sulfate. The solvent was then evaporated. Ethanol was added to the residue to crystallize it. The crystals were then recrystrallized from ethyl acetate to give 2.4 g (2S)-(+)-(5-chloro-2-cyanophenoxy)-2,3-epoxypropane.

後処理

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was then evaporated
  4. additionEthanol was added to the residue
  5. customto crystallize it

出典と根拠

ORDレコード
ord-b591801eab71441b9a149272edd4de53
出典データセット
uspto-grants-1992_07
特許番号
US05130314

反応ノート

読み込み中…