Methyl 3-nonynoate → Methyl 3-nonenoate

HRID 1606684노트

반응식

HRID 1606684 반응식
[C:1]([O:11][CH3:12])(=[O:10])[CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[H][H]>S([O-])([O-])(=O)=O.[Ba+2].[Pd+2].S([O-])([O-])(=O)=O.N1C=CC=CC=1>[C:1]([O:11][CH3:12])(=[O:10])[CH2:2][CH:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

참가 물질

5

반응물 2

HCID 548868Methyl 3-nonynoateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 61631Methyl 3-nonenoate

시약·촉매·용매 2

HCID 17887766Palladium barium sulphate촉매HCID 1049Pyridine용매

실험 절차

A mixture of 5 g. of 1-bromo-2-octyne, 7 g. of potassium cyanide and 35 ml. of dimethylsulfoxide is stirred and heated under nitrogen for about 2.5 hrs. at reflux temperature. The mixture is then poured into water and extracted with ether. The ether extract is washed with water, than with saturated aqueous sodium chloride, dried over sodium sulfate, and evaporated under reduced pressure leaving a residue comprising 3-nonynenitrile. The thus obtained residue is mixed with 45 ml. of 25% hydrogen chloride in methanol containing 0.5 ml. of water while cooling in an ice bath. The ice is allowed to melt and the mixture is stirred for about 18 hrs., then is poured into water and extracted with ether. The ether extract is washed with water, aqueous sodium bicarbonate, and saturated aqueous sodium chloride, dried over sulfate, and evaporated under reduced pressure leaving a residue comprising methyl 3-nonynoate. A mixture of the thus obtained methyl 3-nonynoate, 500 mg. of 5% palladium-barium sulfate catalyst and 40 ml. of pyridine is shaken under hydrogen for about 2 hrs., until the uptake of hydrogen practically ceases. The mixture is then filtered, diluted with water, and extracted with ether. The ether extract is washed with water, dilute hydrochloric acid, and aqueous sodium bicarbonate, then is dried over sodium sulfate and evaporated to leave a residue comprising methyl 3-nonenoate.

후처리

  1. filtrationThe mixture is then filtered
  2. additiondiluted with water
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washis washed with water, dilute hydrochloric acid, and aqueous sodium bicarbonate
  6. dry with materialis dried over sodium sulfate
  7. customevaporated

출처 및 근거

ORD 기록
ord-4f2deb69651840ceb0a6858791d31f22
출처 데이터셋
uspto-grants-1976_04
특허 번호
US03953499

반응 노트

불러오는 중…