Diethyl Ether → alpha-Methyl-4-(3-pyridylmethyl)benzyl alcohol

HRID 2058517Notes

Reaction equation

HRID 2058517 reaction equation
C[Mg]I.COC(=O)/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:11][CH:10]=1.[Cl-].[NH4+].C([O:27]CC)C>O1CCCC1>[CH3:7][CH:8]([OH:27])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 12882181(E)-3-[4-(3-Pyridylmethyl)phenyl]acrylic acid methyl esterHCID 178418373HCID 178418373, compound

Product 1

HCID 12904574alpha-Methyl-4-(3-pyridylmethyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atomsphere of nitrogen, 1.5 ml of a 3M solution of methylmagnesium iodide in diethyl ether were added to a solution of 830 mg of the aldehyde(prepared as described in Reference Example 1) in 20 ml of tetrahydrofuran at -70° C., the mixture was allowed to warm from -70° C. to room temperature over a period of one hour with stirring, poured into a saturated aqueous solution of ammonium chloride, and extracted with diethyl ether. The extract was washed with water, and a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:1) as eluent to give 547 mg of the title compound having the following physical characteristics:

Workup

  1. temperatureto warm from -70° C. to room temperature over a period of one hour
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of cyclohexane and ethyl acetate (1:1) as eluent

Sources & evidence

ORD record
ord-3616b10d8a874c48aef8a7a793a11ca6
Source dataset
uspto-grants-1982_03
Patent number
US04317828

Reaction notes

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