Water → HCID 66747471, compound

HRID 331687Notes

Reaction equation

HRID 331687 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]#N)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Br-].[Mg+2].[Br-].[Cl-].[NH4+].[OH2:19].[O:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[CH2:24]([O:20][C:2]1[CH:3]=[C:4]([C:12]([C:8]2([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:11][CH2:10][CH2:9]2)=[O:19])[CH:5]=[CH:6][CH:7]=1)[C:23]1[CH:11]=[CH:8][CH:9]=[CH:21][CH:22]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 82241Magnesium BromideHCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrile

Product 1

HCID 66747471HCID 66747471, compound

Procedure

To a solution of 1-(4-chlorophenyl)cyclobutanecarbonitrile (2.5 g, 13 mmol) in tetrahydrofuran was added at −5° C. under nitrogen 4-(benzyloxy)phenyl)magnesium bromide (1 M, 39 ml, 39 mmol). The mixture was stirred over night at room temperature. A saturated solution of ammonium chloride and water was added. The organic layer was separated, and the aqueous layer extracted with diethyl ether. The combined organic layers were dried (sodium sulfate) and the solvent evaporated. Purification on SiO2 afforded 3.3 g of desired product as colorless oil.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with diethyl ether
  3. dry with materialThe combined organic layers were dried (sodium sulfate)
  4. customthe solvent evaporated
  5. customPurification on SiO2

Sources & evidence

ORD record
ord-9164ddf271e34806b643233e5f30f596
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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