4-Chlorobutyrophenone → HCID 59190385, compound

HRID 219624

Reaction equation

HRID 219624 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[CH3:13][C:14](=[CH2:18])[CH2:15][Mg]Cl>C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([OH:6])[CH2:15][C:14]([CH3:18])=[CH2:13]

Participants

4

Reactant 2

HCID 2535334-ChlorobutyrophenoneHCID 178448200HCID 178448200, compound

Product 1

HCID 59190385HCID 59190385, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 4-chloro-1-phenylbutan-1-one (3.64 g, 0.02 mol) in THF (60 mL) was added (2-methylallyl)magnesium chloride (60 mL, 1 mol/L) at −78° C. The mixture was stirred at room temperature for 1 h. TLC showed the disappearance of the starting material. The mixture was quenched with satd aq NH4Cl and extracted with EtOAc. The combined organic phase was dried over Na2SO4 and concentrated to give the crude final product, which was purified by chromatography to afford the compound 7-chloro-2-methyl-4-phenylhept-1-en-4-ol (4.2 g, 90%).

Workup

  1. customThe mixture was quenched with satd aq NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude final product, which
  6. customwas purified by chromatography

Sources & evidence

ORD record
ord-2ce09fc72c3c43fb97a37619c012f5cd
Source dataset
uspto-grants-2012_06
Patent number
US08202857B2

Linked notes

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