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

Reaction equation

HRID 922268 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-b221ad47576d4438b29f562d6346b4b9
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Linked notes

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