Tetrahydrofuran → 1-Chlor-5-methyl-3-phenylhex-5-en-3-ol

HRID 884351Notes

Reaction equation

HRID 884351 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[NH4+].[Cl-].C1COCC1.Br[CH2:20][C:21]([CH3:23])=[CH2:22]>CCOC(C)=O.[Zn]>[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([OH:5])[CH2:22][C:21]([CH3:23])=[CH2:20]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 702953-ChloropropiophenoneHCID 3577853-Bromo-2-methyl-1-propene

Product 1

HCID 595323881-Chlor-5-methyl-3-phenylhex-5-en-3-olYield 65.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a well stirred mixture of 3-chloropropiophenone (10.0 g, 59.3 mmol), zinc powder (4.0 g, 1.03 equiv), satd aq NH4Cl solution (150 mL), THF (70 mL), a solution of the 3-bromo-2-methylprop-1-ene (16 g, 2 equiv) was added slowly. The reaction was exothermic mildly. After the addition, the mixture was heated to reflux for 1.5 h. After being cooled to rt, the mixture was diluted with EtOAc (200 mL), separated, washed with brine (35 mL), and dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 120 g silica gel column, eluted with a 0-10% methanol in CH2Cl2 gradient, to afford 1-chloro-5-methyl-3-phenylhex-5-en-3-ol (8.67 g product, 65% yield).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1.5 h
  4. customseparated
  5. washwashed with brine (35 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration and concentration
  8. customthe residue was purified by chromatography on a 120 g silica gel column
  9. washeluted with a 0-10% methanol in CH2Cl2 gradient

Sources & evidence

ORD record
ord-5a3199f9d7354c049f36068a07253c7f
Source dataset
uspto-grants-2012_08
Patent number
US08242111B2

Reaction notes

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