Cyanic acid → Tetrahydropyranyl ether

HRID 64922

反応式

HRID 64922 の反応式
[C:1]([OH:3])#N.[O:4]1[CH:9]=[CH:8][CH2:7][CH2:6][CH2:5]1.[C:10]1(C)C=C[C:13](S(O)(=O)=O)=[CH:12][CH:11]=1.CC[O:23]CC>C(Cl)Cl>[O:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[O:23][CH:13]1[CH2:12][CH2:11][CH2:10][CH2:1][O:3]1

参加物

6

反応物 4

HCID 540Cyanic acidHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyran

生成物 1

HCID 263182Tetrahydropyranyl ether

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 1.23 g of Part F cyano-alcohol (7.36 mmole) in 20 ml of dry methylene chloride was treated with 800 ml of dihydropyran (8.89 mmole) and catalytic amount of p-toluene sulfonic acid at 0°-5° C. After 4 hours, the reaction mixture was diluted with ether and washed with aqueous sodium bicarbonate solution. The aqueous layer was reextracted twice with ether. The combined organic extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude residue was chromatographed on a silica gel column and eluted with 20-25% ethyl acetate in hexane to obtain 1.61 g of title tetrahydropyranyl ether.

後処理

  1. washwashed with aqueous sodium bicarbonate solution
  2. extractionThe combined organic extract
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was chromatographed on a silica gel column
  6. washeluted with 20-25% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-8d26df4c844841088d52bed2ea1d89a7
出典データセット
uspto-grants-1986_09
特許番号
US04611006

関連ノート

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