Ammonium Chloride → HCID 18417946, compound

HRID 2037188Notes

Reaction equation

HRID 2037188 reaction equation
CON(C)[C:4]([C:6]1([CH3:14])[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[O:8][CH2:7]1)=[O:5].[CH3:16][Mg]Br.[Cl-].[NH4+]>C1COCC1>[CH3:13][C:9]1([CH3:12])[O:8][CH2:7][C:6]([C:4](=[O:5])[CH3:16])([CH3:14])[CH2:11][O:10]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 15173281HCID 15173281, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 18417946HCID 18417946, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of N-methoxy-N,2,2,5-tetramethyl-1,3-dioxane5-carboxylic acid amid (1.07 g, 4.92 mmol) and THF (10 mL) was gradually added 3 mol/L methylmagnesium bromide in THF (2.46 mL, 7.4 mmol) at 0° C. under nitrogen atmosphere, and the resulting mixture was stirred at 0° C. for 4 hours. After the reaction was completed, saturated ammonium chloride aqueous solution was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulphate, and concentrated in vacuo to give 1-(2,2,5-trimethyl-1,3-dioxane5-yl)ethanone (0.76 g, yield: 90%) as colorless oil.

Workup

  1. customat 0° C.
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71e8852559874cb980b16eb4e98b8d8b
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

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