Cyanic acid → Tetrahydropyranyl ether

HRID 64660노트

반응식

HRID 64660 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 263182Tetrahydropyranyl ether

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7c06ee9a76c54773bc41e1e120fe8f16
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04609671

반응 노트

불러오는 중…