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

반응식

HRID 922268 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 25517Ammonium Chloride용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-b221ad47576d4438b29f562d6346b4b9
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278915B2

연결된 노트

불러오는 중…