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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
ノート
印刷プレビュー

反応式

HRID 2268211 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7761Diethyl MalonateHCID 8028Tetrahydrofuran2 回HCID 24758Sodium hydrideHCID 70213311Allyl 3-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyloxy]benzoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c9b5c5a48b184ae58264c72f3a8892db
出典データセット
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06326510B1

反応ノート

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