5-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → HCID 66685166, compound

HRID 922276Notes

Reaction equation

HRID 922276 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]=[C:7]2[C:12](=[O:13])[O:11][C:10]([CH3:15])([CH3:14])[O:9][C:8]2=[O:16])=[CH:4][CH:3]=1.[CH:19]1([Mg]Br)[CH2:21][CH2:20]1>C1COCC1>[CH:19]1([C:6]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:18][CH:17]=2)=[C:7]2[C:8](=[O:16])[O:9][C:10]([CH3:15])([CH3:14])[O:11][C:12]2=[O:13])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 3705415-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 178418630HCID 178418630, compound

Product 1

HCID 66685166HCID 66685166, compoundYield 42.76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 250 mL RB flask fitted with magnetic stirrer was charged 6 mL of dry THF under argon atmosphere. To the stirred solvent was added 5-(4-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (0.6 g, 2.41 mmol). The resulting mixture was cooled to 0° C. and was added cyclopropylmagnesium bromide (25 mL, 0.5 M in THF, 7.25 mmol). The resulting mixture was stirred at ambient temperatures for 2 h. Then, the reaction mass was quenched with 20 mL of 1N HCl then, ethyl acetate (50 mL) was added, stirred well and the layers were separated. The organic layer was washed with water (100 mL×3), brine solution. Then the organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the resulting crude compound is purified by column chromatography on silica gel (60-120 meshes) using petroleum ether (60-80) and ethyl acetate as eluent. The product was obtained as yellow solid. Yield: 42.76% (0.3 g) MS (ESI, 120 ev): m/z=291.1 (M+1). (300 MHz, DMSO-d6): δ 9.16 (s, 1H), 6.95-6.98 (d, 2H), 6.53-6.56 (d, 2H), 4.42-4.43 (d, 1H), 2.54-2.59 (m, 1H), 1.61 (s, 4H), 1.29 (s, 3H), 0.40-0.49 (m, 2H), 0.23-0.28 (m, 1H), 0.03-0.01 (m, 1H).

Workup

  1. customTo a 250 mL RB flask fitted with magnetic stirrer
  2. customThen, the reaction mass was quenched with 20 mL of 1N HCl
  3. additionethyl acetate (50 mL) was added
  4. stirringstirred well
  5. customthe layers were separated
  6. washThe organic layer was washed with water (100 mL×3), brine solution
  7. dry with materialThen the organic layer was dried over anhydrous Na2SO4
  8. customThe solvent was removed under reduced pressure
  9. customthe resulting crude compound is purified by column chromatography on silica gel (60-120 meshes)
  10. customThe product was obtained as yellow solid

Sources & evidence

ORD record
ord-c0987574ca094c67beacb4c6be1b83a8
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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