Methanol → 1-Hydroxy-3-(3-ethyl-1-methylcyclobutyl)-prop-1-en-3-one

HRID 27299

반응식

HRID 27299 반응식
[H-].[Na+].[CH:3](OC)=[O:4].[CH3:7][C:8]([C:10]1([CH3:16])[CH2:13][CH:12]([CH2:14][CH3:15])[CH2:11]1)=[O:9].CO>CCCCCC.CCOCC>[OH:4][CH:3]=[CH:7][C:8]([C:10]1([CH3:16])[CH2:13][CH:12]([CH2:14][CH3:15])[CH2:11]1)=[O:9]

참가 물질

7

반응물 4

HCID 887MethanolHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 53858413(1-Methyl-3-ethylcyclobutyl) methyl ketone

생성물 1

HCID 705764901-Hydroxy-3-(3-ethyl-1-methylcyclobutyl)-prop-1-en-3-one

시약·촉매·용매 2

HCID 3283Diethyl Ether용매3회HCID 8058Hexane용매

실험 절차

Sodium hydride (1.25 g of 50% mineral oil dispersion, 50 mmol) was washed with dry hexane and then stirred under an argon atmosphere with 12.5 ml of dry ether. A solution of 5 ml of methyl formate and 2.4 g of (1-methyl-3-ethylcyclobutyl) methyl ketone (prepared in Example 3A) in 5 ml of ether was then added to the reaction mixture along with about 0.5 ml of methanol. As a voluminous precipitate formed, sufficient ether was added to make the reaction mixture more easily stirred. The resultant mixture was stirred for 1 hr and then quenched by the addition of water. The ether phase was separated and extracted three times with 1 M sodium hydroxide. The combined aqueous extraction phases were acidified with concentrated hydrochloric acid and extracted three times with ether. The combined ether extract was evaporated in vacuo. Traces of water were removed by twice addition of benzene which was removed by evaporation in vacuo. The title compound had the following physical characteristics:

후처리

  1. customAs a voluminous precipitate formed
  2. customquenched by the addition of water
  3. customThe ether phase was separated
  4. extractionextracted three times with 1 M sodium hydroxide
  5. extractionextracted three times with ether
  6. extractionThe combined ether extract
  7. customwas evaporated in vacuo
  8. customTraces of water were removed by twice addition of benzene which
  9. customwas removed by evaporation in vacuo

출처 및 근거

ORD 기록
ord-09d28b60d30b4a19968902f263805978
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220795

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