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

HRID 346274
ノート
印刷プレビュー

反応式

HRID 346274 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].[CH:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)=[O:21]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.CN(C)C=O>[C:26]([C:25]1[CH:30]=[CH:31][C:22]([C:20](=[O:21])[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:23][CH:24]=1)([O:28][CH3:29])=[O:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 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 6228
Dimethylformamide
溶媒

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 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. 2-(4-Carbomethoxyphenyl)-5-(5,6,7,8-tetrahy-dro-5,5,8,8-tetramethyl-2-naphthalenyl)-thiophene:

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-9d07dbe3191c4f18ad954efa97c1f00e
出典データセット
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05061705

反応ノート

読み込み中…

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