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 1993081Notes

Reaction equation

HRID 1993081 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-c7e07b3ee30f47bcb6e10e3d45f14e34
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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