Diethyl Carbonate → Ethyl 7-methoxy-1-oxo-3,4-dihydro-2H-naphthalene-2-carboxylate

HRID 654234노트

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HRID 654234 반응식
COC1C=C2C(CCC(C(O)=O)C2)=CC=1.[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([CH2:22][CH2:23][CH2:24][C:25]2=[O:28])=[CH:20][CH:19]=1.[CH2:29]([O:31][C:32](=O)[O:33]CC)[CH3:30].[H-].[Na+]>O1CCCC1.O.C(O)(=O)C>[CH2:29]([O:31][C:32]([CH:24]1[CH2:23][CH2:22][C:21]2[C:26](=[CH:27][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[C:25]1=[O:28])=[O:33])[CH3:30]

참가 물질

8

반응물 4

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-oneHCID 147228197-Methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

생성물 1

HCID 10848142Ethyl 7-methoxy-1-oxo-3,4-dihydro-2H-naphthalene-2-carboxylate수율 96.4%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
60 °C

실험 절차

The starting 7-methoxy-1,2,3,4-tetrahydronaphthalen-2-carboxylic acid, which is a known product, can be prepared as follows: a solution of 7-methoxy-3,4-dihydronaphthalene-1(2H)-one (66.4 g, 0.376 mol) in anhydrous tetrahydrofuran (350 ml) is added in 1 hour to a mixture of distilled diethylcarbonate (116 ml, 0.957 mol), 80% sodium hydride (39.7 g, 1.32 mol) and anhydrous tetrahydrofuran (350 ml) heated to 60° C. The thus obtained reaction mixture is refluxed for 4 hours and then cooled. Acetic acid is then added dropwise up to acidic pH and water is added until complete dissolution of the precipitate occurs. The solution is extracted with ethyl ether, the organic phase is washed with water and with a sodium bicarbonate solution, dried and evaporated to dryness. The thus obtained oily product is purified by distillation under reduced pressure yielding 90 g of 7-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-carboxylic acid ethyl ester. B.p.0.4 mmHg 160°-165° C.

후처리

  1. customcan be prepared
  2. customThe thus obtained reaction mixture
  3. temperatureis refluxed for 4 hours
  4. temperaturecooled
  5. additionis added until complete dissolution of the precipitate
  6. extractionThe solution is extracted with ethyl ether
  7. washthe organic phase is washed with water and with a sodium bicarbonate solution
  8. customdried
  9. customevaporated to dryness
  10. distillationThe thus obtained oily product is purified by distillation under reduced pressure

출처 및 근거

ORD 기록
ord-b7b217498f464c609302d6871c45166e
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05130339

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