Hydrochloric Acid → HCID 17978856, compound

HRID 1591805Notes

Reaction equation

HRID 1591805 reaction equation
[CH2:1]([Br:3])[CH3:2].[Mg:4].[O:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([O:20][Si](C)(C)C)[C:18]#N)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.Cl.CC[O:28]CC>>[CH2:17]([Mg:4][Br:3])[CH3:18].[OH:20][CH:17]([C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][O:5][CH2:6][CH2:7]2)=[CH:12][CH:13]=1)[C:18](=[O:28])[CH2:1][CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 6332Ethyl BromideHCID 5462224Magnesium2×HCID 17978855HCID 17978855, compound

Product 2

HCID 17978856HCID 17978856, compoundHCID 178418443HCID 178418443, compound

Conditions

Temperature
0 °C

Procedure

Ethyl magnesium bromide in ether is prepared by slowly adding a solution of ethyl bromide in ether to magnesium at slight reflux. When all the magnesium is dissolved, the solution is cooled to 0° C. and a solution of one equivalent of 2-(4-morpholinophenyl)2-trimethylsilyloxy-ethanenitrile (prepared according to step 1.1) is slowly added. The reaction mixture is kept at room temperature for two hours and subsequently heated to reflux for a further five hours. After cooling the reaction mixture is poured onto a mixture of 2M HCl and ice. The suspension is efficiently stirred at room temperature overnight. The organic layer is separated, the water phase extracted with dichloromethane and the combined organic extracts washed with brine and dried over magnesium sulfate. Evaporation of the solvent and chromatography on silica gel (hexane/ethyl acetate 4:1) gives 1-hydroxy-1-(4-morpholinophenyl)-butan-2-one.

Workup

  1. temperaturesubsequently heated
  2. temperatureto reflux for a further five hours
  3. temperatureAfter cooling the reaction mixture
  4. customThe organic layer is separated
  5. extractionthe water phase extracted with dichloromethane
  6. washthe combined organic extracts washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customEvaporation of the solvent and chromatography on silica gel (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-0d817b6b99b741208fe4daf0a28faa75
Source dataset
uspto-grants-2007_11
Patent number
US07291654B2

Reaction notes

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