Water → (4-Cyclopropylphenyl)-(3-hydroxy-5-methylthiophen-2-yl)methanone

HRID 554559Notes

Reaction equation

HRID 554559 reaction equation
C(Cl)Cl.B(Cl)(Cl)Cl.[CH:8]1([C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:19]3[S:20][C:21]([CH3:26])=[CH:22][C:23]=3[O:24]C)=[O:18])=[CH:13][CH:12]=2)[CH2:10][CH2:9]1.O>C(Cl)Cl>[CH:8]1([C:11]2[CH:12]=[CH:13][C:14]([C:17]([C:19]3[S:20][C:21]([CH3:26])=[CH:22][C:23]=3[OH:24])=[O:18])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 20463568Boron trichloride methylene chlorideHCID 67460209(4-Cyclopropylphenyl)-(3-methoxy-5-methylthiophen-2-yl)methanone

Product 1

HCID 136413718(4-Cyclopropylphenyl)-(3-hydroxy-5-methylthiophen-2-yl)methanoneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, a boron trichloride methylene chloride solution (1.0 M, 6.4 mL, 6.4 mmol) was added to a solution of (4-cyclopropylphenyl)-(3-methoxy-5-methylthiophen-2-yl)methanone (582 mg, 2.14 mmol) in methylene chloride (12 mL) at −15° C. and the reaction mixture was stirred for one hour. Water was added thereto and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=methanol:methylene chloride (1:100)] to obtain the title compound (497 mg, 90%).

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. distillationthe solvent was distilled under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [developing solution=methanol:methylene chloride (1:100)]

Sources & evidence

ORD record
ord-b7e026c90fbc4c76a6d27c9299a0ff73
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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