Triethylamine → 1-(4-Carbomethoxyphenyl)-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-butane-1,4-dione

HRID 1614387

反応式

HRID 1614387 の反応式
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]2([CH3:19])[CH3:18])=[O:5].C(N(CC)CC)C.[CH:27]([C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1)=[O:28]>CN(C)C=O.[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1>[C:33]([C:32]1[CH:37]=[CH:38][C:29]([C:27](=[O:28])[CH2:2][CH2:3][C:4]([C:6]2[CH:15]=[CH:14][C:13]3[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]([CH3:19])([CH3:18])[C:8]=3[CH:7]=2)=[O:5])=[CH:30][CH:31]=1)([O:35][CH3:36])=[O:34]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 15294Methyl 4-FormylbenzoateHCID 147265116-(3-Chloropropionyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene

生成物 1

HCID 147264921-(4-Carbomethoxyphenyl)-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-butane-1,4-dione収率 45.5%

試薬・触媒・溶媒 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride触媒HCID 6228Dimethylformamide溶媒2 回

実験手順

5.6 g (0.02 mole) of 6-(3-chloropropionyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnapthalene and 3.3 ml (0.024 mole) of triethylamine in 30 ml of dimethylformamide were stirred for 1 hour at room temperature. Thereafter, a solution of 3.6 g (0.025 mole) of methyl 4-formylbenzoate and 1 g of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride in 10 ml of dimethylformamide was added dropwise. Stirring was continued for 1 hour, after which the mixture was poured onto ice/water and extracted twice with ethyl acetate, and the combined organic extracts were washed several times with water, dried over magnesium sulfate and evaporated down. 3.7 g of 1-(4-carbomethoxyphenyl)-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-butane-1,4-dione of melting point 139°-141° C. were obtained from the residue (6.4 g) after recrystallization from ethanol.

後処理

  1. additionafter which the mixture was poured onto ice/water
  2. extractionextracted twice with ethyl acetate
  3. washthe combined organic extracts were washed several times with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down

出典と根拠

ORDレコード
ord-8a5f191313e74a6687ed041f495303a4
出典データセット
uspto-grants-1993_03
特許番号
US05196532

関連ノート

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