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

HRID 2070543Notes

Reaction equation

HRID 2070543 reaction equation
[C:1]([Mg]Br)#[C:2][CH3:3].[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.[Cl-].[NH4+].CCCCCC>O1CCCC1>[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:1]#[C:2][CH3:3])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 3705415-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 178419101HCID 178419101, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0.5M tetrahydrofuran solution of 1-propynylmagnesium bromide (800 mL) was added dropwise a solution of 5-(4-hydroxybenzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dion e (47.3 g) obtained in Substep 1 in tetrahydrofuran (650 mL) under argon atmosphere at 11° C. over 40 minutes, followed by stirring the reaction mixture at room temperature for 1 hour. Then, to the reaction mixture were added successively aqueous ammonium chloride solution (34 g/l L) and hexane (1 L), followed by removing the organic layer. After adding saturated aqueous potassium hydrogen sulfate solution to the aqueous layer and adjusting a pH to 1, the aqueous layer was extracted with ethyl acetate twice. The organic layer was dried and concentrated to give 5-[1-(4-hydroxyphenyl)-but-2-ynyl]-2,2-dimethyl-[1,3]dioxan e-4,6-dione (54.8 g).

Workup

  1. customby removing the organic layer
  2. additionAfter adding saturated aqueous potassium hydrogen sulfate solution to the aqueous layer
  3. extractionthe aqueous layer was extracted with ethyl acetate twice
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c0dd1813f9644ea0a150e541244b1f50
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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