5-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 5-(1-(4-Hydroxyphenyl)but-2-yn-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 922268

反応式

HRID 922268 の反応式
Br[Mg][C:3]#[C:4][CH3:5].[OH:6][C:7]1[CH:23]=[CH:22][C:10]([CH:11]=[C:12]2[C:17](=[O:18])[O:16][C:15]([CH3:20])([CH3:19])[O:14][C:13]2=[O:21])=[CH:9][CH:8]=1.OS([O-])(=O)=O.[K+]>C1COCC1.[NH4+].[Cl-].CCCCCC>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([CH:11]([CH:12]2[C:13](=[O:21])[O:14][C:15]([CH3:20])([CH3:19])[O:16][C:17]2=[O:18])[C:3]#[C:4][CH3:5])=[CH:22][CH:23]=1

参加物

7

反応物 3

HCID 3705415-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 516920Potassium bisulfateHCID 178419101HCID 178419101、化合物

生成物 1

HCID 598551335-(1-(4-Hydroxyphenyl)but-2-yn-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione収率 100%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To a 250 mL 3-necked RB flask fitted with magnetic stirrer was charged with bromo(prop-1-yn-1-yl)magnesium (42.5 mL, 211 mmol) in THF (30 mL). To the RM was added slowly 5-(4-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (5.0 g, 100.8 mmol) in THF (20 mL) under nitrogen atmosphere. The RM was stirred at room temperature about 30 minutes. The reaction mixture was diluted with NH4Cl solution and hexane. The aqueous layer was acidified with KHSO4 solution to adjust the pH 2 and extracted with ethyl acetate, washed with water, then dried to obtain the product (5.8 g, yield: 100.0%).

後処理

  1. customTo a 250 mL 3-necked RB flask fitted with magnetic stirrer
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. customdried

出典と根拠

ORDレコード
ord-b221ad47576d4438b29f562d6346b4b9
出典データセット
uspto-grants-2016_03
特許番号
US09278915B2

関連ノート

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