Chloroform → HCID 136342974, compound

HRID 1993810Notes

Reaction equation

HRID 1993810 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1[O:11][C:12]([CH:27]([CH3:29])[CH3:28])=[C:13]([CH2:15][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH3:26])[CH:20]=2)=[O:18])[N:14]=1.B(Cl)(Cl)Cl.C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1[O:11][C:12]([CH:27]([CH3:29])[CH3:28])=[C:13]([CH2:15][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH3:26])[CH:20]=2)=[O:18])[N:14]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 12993440HCID 12993440, compound

Product 1

HCID 136342974HCID 136342974, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The obtained 3-[2-(2-methoxy-4-chlorophenyl)-5-isopropyl-4-oxazolyl]-1-(3-methyl-4-hydroxyphenyl)propan-1-one (621 mg, 1.50 mmol) was suspended in methylene chloride (30 mL) and cooled with ice. To the suspension, a 1M methylene chloride solution of boron trichloride (BCl3) (3.0 mL, 3.00 mmol) was dropwise added for 1 minute. The mixture was allowed to room temperature, stirred for 72 hours, and poured into ice water. Chloroform and saturated sodium hydrogen carbonate were added to the mixture. The organic layer was washed with water, and a saline, dried over anhydrous sodium sulfate. The chloroform was removed under reduced pressure. The residue was purified by column chromatography on silica gel with hexane/ethyl acetate (3/1) to give the desired compound (385 mg) as colorless oil (yield 64%).

Workup

  1. temperaturecooled with ice
  2. customwas allowed to room temperature
  3. washThe organic layer was washed with water
  4. dry with materiala saline, dried over anhydrous sodium sulfate
  5. customThe chloroform was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel with hexane/ethyl acetate (3/1)

Sources & evidence

ORD record
ord-c475a2e903a64cba8ea81d4342dc4603
Source dataset
uspto-grants-2010_01
Patent number
US07652045B2

Reaction notes

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