HCID 10200962, compound → HCID 10273345, compound

HRID 842107Notes

Reaction equation

HRID 842107 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[CH2:10][C:11]2[O:12][C:13]3[C:19]([CH2:20][CH:21]=[O:22])=[CH:18][C:17]([Cl:23])=[CH:16][C:14]=3[N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)=[O:31].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[CH2:10][C:11]2[O:12][C:13]3[C:19]([CH2:20][C:21]([OH:31])=[O:22])=[CH:18][C:17]([Cl:23])=[CH:16][C:14]=3[N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10200962HCID 10200962, compoundHCID 131709961Jones' reagent

Product 1

HCID 10273345HCID 10273345, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-(3-cyclopentyloxy-4-methoxybenzyl)-5-chlorobenzoxazole-7-ethanal (2.0 g, 0.005 mol) in 50 ml of acetone was treated with 20 ml of 1 N Jones reagent and stirred for 1 hour at room temperature. Excess Jones reagent was destroyed by the addition of 50 ml of 2-propanol and the low boiling solvents were stripped under reduced pressure. Water (50 ml) and saturated sodium chloride (50 ml) were added and the aqueous residue was extracted with 2×75 ml of ethyl acetate. After drying, the ethyl acetate was evaporated to give 2.1 g of a brown foam. Solution of this material in CH2Cl2 and flash chromatography on silica gel afforded 0.72 g of the title acid as a yellow foam after elution with 500 ml of 0.5% CH3OH in CH2Cl2. The foam was dissolved in 3 ml of CH3OH and allowed to crystallize for 1 hour at freezer temperatures. After filtration, a total of 0.27 g of yellow title compound, mp 131-133° C., was isolated.

Workup

  1. customExcess Jones reagent was destroyed by the addition of 50 ml of 2-propanol
  2. additionWater (50 ml) and saturated sodium chloride (50 ml) were added
  3. extractionthe aqueous residue was extracted with 2×75 ml of ethyl acetate
  4. customAfter drying
  5. customthe ethyl acetate was evaporated

Sources & evidence

ORD record
ord-25301a0cde7543198b565e6c1e5ec15f
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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