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Diethyl Malonate → 3-[3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]benzoic acid

HRID 2268211
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인쇄 미리보기

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HRID 2268211 반응식
[H-].[Na+].C1COCC1.C(OCC)(=O)CC(OCC)=O.[CH3:19][C:20]1([CH3:49])[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:26]2[CH:25]=[C:24]([CH:32]=[CH:33][C:34]([O:36][C:37]3[CH:38]=[C:39]([CH:46]=[CH:47][CH:48]=3)[C:40]([O:42]CC=C)=[O:41])=[O:35])[CH:23]=[CH:22][C:21]1=2>O>[CH3:19][C:20]1([CH3:49])[CH2:29][CH2:28][C:27]([CH3:30])([CH3:31])[C:26]2[CH:25]=[C:24]([CH:32]=[CH:33][C:34]([O:36][C:37]3[CH:38]=[C:39]([CH:46]=[CH:47][CH:48]=3)[C:40]([OH:42])=[O:41])=[O:35])[CH:23]=[CH:22][C:21]1=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7761Diethyl MalonateHCID 8028Tetrahydrofuran2회HCID 24758Sodium hydrideHCID 70213311Allyl 3-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]benzoate

생성물 1

HCID 702158333-[3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]benzoic acid

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

210 mg (6.8 mmol) of sodium hydride (80% in oil) and 15 ml of THF are introduced into a round-bottomed flask under a stream of nitrogen. 1 ml (6.8 mmol) of diethyl malonate is then added dropwise and the mixture is stirred until the evolution of gas has ceased. This solution is introduced dropwise into a mixture of 2.6 g (6.2 mmol) of allyl 3-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]-benzoate, 50 ml of THF and 400 mg of tetrakis-(triphenylphosphine)palladium(0) and the mixture is stirred at room temperature for three hours. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of ethyl ether and hexane (50/50). After evaporating the solvents, 1.5 g (64%) of 3-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]-benzoic acid, with a melting point of 134-5° C., are collected.

후처리

  1. stirringthe mixture is stirred at room temperature for three hours
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of ethyl ether and hexane (50/50)
  9. customAfter evaporating the solvents, 1.5 g (64%) of 3-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]-benzoic acid
  10. customwith a melting point of 134-5° C., are collected

출처 및 근거

ORD 기록
ord-c9b5c5a48b184ae58264c72f3a8892db
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326510B1

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