m-Chloroperbenzoic acid → Hexahydro-2H-3,5-methanocyclopenta[b]furan-6-ol

HRID 1375321ノート

反応式

HRID 1375321 の反応式
[OH:1][CH2:2][CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2.ClC1C=CC=C(C(OO)=[O:18])C=1>C(Cl)Cl>[OH:18][CH:6]1[CH:5]2[CH:4]3[CH:3]([CH2:8][CH:7]1[CH2:9]3)[CH2:2][O:1]2

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanol

生成物 1

HCID 12850947Hexahydro-2H-3,5-methanocyclopenta[b]furan-6-ol収率 72.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

12.4 g of 5-hydroxy methyl-2-norbornene and 300 ml of methylene chloride were put in a flask, and 28.7 g (75% content) of m-chloro perbenzoic acid was dropped therein at 30° C. After completion of dropping, it was agitated at the temperature for 1 hour, then it was cooled to 0° C., and the precipitated benzoic acid was removed by filtration. The filtrate was washed with an aqueous solution of sodium sulfite, an aqueous solution of sodium bicarbonate, and then the organic layer was concentrated under a reduced pressure. The resultant crude 2,3-epoxy-5-hydroxy methyl norbornane, 100 ml of toluene and a catalytic amount of a concentrated sulfuric acid were put in a flask, and agitated at 50° C. for 2 hours. Then, usual after-treatment was carried out to yield 10.1 g of 2-hydroxy-4-oxatricyclo[4.2.1.03,7]nonane.

後処理

  1. customat 30° C
  2. customthe precipitated benzoic acid was removed by filtration
  3. washThe filtrate was washed with an aqueous solution of sodium sulfite
  4. concentrationan aqueous solution of sodium bicarbonate, and then the organic layer was concentrated under a reduced pressure
  5. customThe resultant crude 2,3-epoxy-5-hydroxy methyl norbornane, 100 ml of toluene and a catalytic amount of a concentrated sulfuric acid were put in a flask
  6. stirringagitated at 50° C. for 2 hours

出典と根拠

ORDレコード
ord-283716c9f1934956ad170815c339ccae
出典データセット
uspto-grants-2007_01
特許番号
US07169541B2

反応ノート

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