Water → 3-Phenoxy-alpha-ethynylbenzylalcohol

HRID 542615

反応式

HRID 542615 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[OH2:12].O1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>>[O:16]([C:15]1[CH:14]=[C:5]([CH:6]([OH:12])[C:1]#[CH:11])[CH:4]=[CH:3][CH:2]=1)[C:17]1[CH:18]=[CH:3][CH:2]=[CH:1][CH:6]=1

参加物

4

反応物 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 312751,4-Dioxane

生成物 1

HCID 129190923-Phenoxy-alpha-ethynylbenzylalcohol

実験手順

A mixture of 10.4 g of (1R, 5S) 6,6-dimethyl-4(R)-[(S)-ethynyl-(3'-phenoxy-phenyl)-methoxy]-3-oxabicyclo-(3,1,0)-hexan-2-one, 1 g of p-toluene sulfonic acid, 80 ml of water and 80 ml of dioxane was refluxed for 2 hours and was evaporated to dryness under reduced pressure. The residue was added to water and the mixture was stirred and was extracted with isopropyl ether. The organic phase was subjected to the usual treatment and was evaporated to dryness under reduced pressure. The 6 g of residue was chromatographed over silica gel and was eluted with a 7-3 benzeneethyl acetate mixture to obtain 5.1 g of (S) 1-(3-phenoxyphenyl)-prop-2-yn-1-ol with a specific rotation of [α]D20 =+10.5° (c=0.63% in benzene).

後処理

  1. temperaturewas refluxed for 2 hours
  2. customwas evaporated to dryness under reduced pressure
  3. additionThe residue was added to water
  4. extractionwas extracted with isopropyl ether
  5. customwas evaporated to dryness under reduced pressure
  6. customThe 6 g of residue was chromatographed over silica gel
  7. washwas eluted with a 7-3 benzeneethyl acetate mixture

出典と根拠

ORDレコード
ord-01bf2b53cd4f4c5d9fe66074b446056b
出典データセット
uspto-grants-1987_04
特許番号
US04658043

関連ノート

読み込み中…