Phenol, 2-(2-propenyloxy)- → (2R)-3-(o-Allyloxyphenoxy)-1,2-epoxypropane

HRID 2288259

反応式

HRID 2288259 の反応式
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])[CH:2]=[CH2:3].[F-].[K+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N+](C1C=C(S(O[CH2:45][C@@H:46]2[O:48][CH2:47]2)(=O)=O)C=CC=1)([O-])=O>C1COCC1.O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:45][C@@H:46]1[O:48][CH2:47]1)[CH:2]=[CH2:3]

参加物

7

反応物 4

HCID 70772Phenol, 2-(2-propenyloxy)-HCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 522689Potassium FluorideHCID 2724141Tetrabutylammonium Fluoride

生成物 1

HCID 40428630(2R)-3-(o-Allyloxyphenoxy)-1,2-epoxypropane収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

o-Allyloxyphenol (1.0 g) was dissolved in THF (10 ml) under nitrogen atmosphere and the solution was cooled to 0° C. Potassium fluoride (1.55 g) and tetrabutyl ammonium fluoride (0.2 g) were added thereto and the mixture was stirred for 1 hour. Then, (R)-glycidyl m-nitrobenzenesulfonate (1.73 g, 99.3% e.e.) was added thereto and the mixture was stirred for 40 hours at the same temperature. After the reaction, water was added to the mixture, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, condensed and the residue was subjected to silica gel chromatography (hexane/ethyl acetate; 3:2) to give 0.96 g of (R)-3-(o-allyloxyphenoxy)-1,2-epoxypropane (yield 70%, optical purity 95.9% e.e.) as a colorless oil.

後処理

  1. stirringthe mixture was stirred for 40 hours at the same temperature
  2. additionwas added to the mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate, condensed

出典と根拠

ORDレコード
ord-06cd52a4587047bb9448f7a73b33c711
出典データセット
uspto-grants-2000_07
特許番号
US06087512

関連ノート

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