3,3-Diethoxypropyne → 5-(4,4-Diethoxy-1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)but-2-ynyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1160332Notes

Reaction equation

HRID 1160332 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[CH:6])[CH3:2].C([Mg]Br)C.[CH3:14][C:15]1([CH3:37])[O:20][C:19](=[O:21])[C:18](=[CH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][O:31]3)=[CH:25][CH:24]=2)[C:17](=[O:36])[O:16]1>C1COCC1>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[C:6][CH:22]([CH:18]1[C:17](=[O:36])[O:16][C:15]([CH3:14])([CH3:37])[O:20][C:19]1=[O:21])[C:23]1[CH:24]=[CH:25][C:26]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)=[CH:27][CH:28]=1)[CH3:2]

Participants

5

Reactant 3

HCID 662853,3-DiethoxypropyneHCID 578018192,2-Dimethyl-5-[4-(tetrahydro-pyran-2-yloxy)-benzylidene]-[1,3]dioxane-4,6-dioneHCID 178418443HCID 178418443, compound

Product 1

HCID 591326145-(4,4-Diethoxy-1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)but-2-ynyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Propiolaldehyde diethyl acetal (5 g, 39 mmol) in anhydrous THF (65 mL) was cooled to −5° C. and treated with ethylmagnesium bromide (39 mmol in 14 mL of anhydrous THF) dropwise over 10 min. After 45 min., the solution of Grignard reagent was added to compound 52.1 in anhydrous THF (50 mL). After stirring 1 h, the reaction was quenched with saturated NH4Cl(aq) (20 mL) and diluted with hexanes (100 mL). After mixing vigorously, the layers were separated and the organic layer discarded. The aqueous layer was acidified and extracted twice with diethyl ether. The combined organic layers were washed with saturated brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was used immediately without further purification. MS ESI (pos.) m/e: 478.3 (M+NH4)+.

Workup

  1. customthe reaction was quenched with saturated NH4Cl(aq) (20 mL)
  2. additiondiluted with hexanes (100 mL)
  3. additionAfter mixing vigorously
  4. customthe layers were separated
  5. extractionextracted twice with diethyl ether
  6. washThe combined organic layers were washed with saturated brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was used immediately without further purification

Sources & evidence

ORD record
ord-86594ef20ca74145bc0b8d1c68850390
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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