Tetrahydrofuran → Cyclopropyl-(3-methoxyphenyl)-(3-pyridinyl)methanol

HRID 1595222Notes

Reaction equation

HRID 1595222 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1.[Cl-].[NH4+].C(OCC)(=O)C.[CH2:25]1[CH2:29]OC[CH2:26]1>>[CH:26]1([C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[OH:10])[CH2:25][CH2:29]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 100361373-(3-Methoxybenzoyl)pyridine

Product 1

HCID 15552043Cyclopropyl-(3-methoxyphenyl)-(3-pyridinyl)methanol

Procedure

To a solution of (3-methoxyphenyl)-(3-pyridinyl)methanone (500 mg) in THF (10 ml) was added 1.1M cyclopropylmagnesium bromide THF solution (2 ml) at 0° C. The reaction mixture was warmed to room temperature, and stirred for 30 minutes. Aqueous ammonium chloride and ethyl acetate were added to the reaction mixture, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was filtered and washed with ethyl acetate-hexane (1:2) to give cyclopropyl-(3-methoxyphenyl)-(3-pyridinyl)methanol (470 mg).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried with magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. filtrationThe residue was filtered
  6. washwashed with ethyl acetate-hexane (1:2)

Sources & evidence

ORD record
ord-b4812e6d00c64d81b33860b9335d5a72
Source dataset
uspto-grants-2001_09
Patent number
US06288083B1

Reaction notes

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