Sodium Hydroxide → 2-(6-Carboxy-2-cis-hexenyl)cyclopent-2-en-1-one

HRID 67004

반응식

HRID 67004 반응식
[H-].[Na+].[Br-].[C:4]([CH2:7][CH2:8][CH2:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:6])=[O:5].[CH:30]([CH2:32][C:33]1[C:34](=[O:38])[CH2:35][CH2:36][CH:37]=1)=O.[OH-].[Na+]>CS(C)=O>[C:4]([CH2:7][CH2:8][CH2:9][CH2:10]/[CH:30]=[CH:32]\[C:33]1[C:34](=[O:38])[CH2:35][CH2:36][CH:37]=1)([OH:6])=[O:5]

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 20465672(5-Oxocyclopent-1-en-1-yl)acetaldehyde

생성물 1

HCID 867329642-(6-Carboxy-2-cis-hexenyl)cyclopent-2-en-1-one

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매3회

실험 절차

A mixture of 0.194 g. (0.007952 mole) of sodium hydride (free of mineral oil) and 5.5 ml. of dimethylsulfoxide is heated to 70° C. until gas evolution ceases under a nitrogen atmosphere. The resulting solution is cooled below room temperature and treated with a solution of 1.400 g. (0.00316 mole) of 4-carboxybutyltriphenyl phosphonium bromide [E. J. Corey et al., J. Am. Chem. Soc., 91, 5675 (1969)] in 6 ml. of dimethylsulfoxide. To the resulting red solution is added 0.00263 mole of 2-formylmethylcyclopent-2-en-1-one (Example 898) in 2 ml of dimethylsulfoxide and the mixture is stirred at room temperature for 2.25 hours. The mixture is poured into ice water, sodium hydroxide solution is added to pH 12, and the neutral materials are extracted with diethyl ether. The basic phase is acidified with dilute hydrochloric acid and is extracted with diethyl ether. The organic phase is washed with water and saturated brine, dried (Na2SO4), and evaporated to a semicrystalline mass. The latter is triturated with hot hexane, the solids are filtered off, and the filtrate is evaporated to yield the subject product as an oil.

후처리

  1. additionA mixture of 0.194 g
  2. temperatureThe resulting solution is cooled below room temperature
  3. additiontreated with a solution of 1.400 g
  4. additionis added to pH 12
  5. extractionthe neutral materials are extracted with diethyl ether
  6. extractionis extracted with diethyl ether
  7. washThe organic phase is washed with water and saturated brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated to a semicrystalline mass
  10. customThe latter is triturated with hot hexane
  11. filtrationthe solids are filtered off
  12. customthe filtrate is evaporated

출처 및 근거

ORD 기록
ord-c4e93aa7a5d34f288b4b8daa110282ef
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04343949

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