Hydrochloric Acid → HCID 86744612, compound

HRID 2254364Notes

Reaction equation

HRID 2254364 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:28])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:18]=2)=[CH:12][C:11]=1[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[BH4-].[Na+].Cl>C(O)C.O.C(OCC)(=O)C>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:18]=2)[OH:28])=[CH:12][C:11]=1[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86744613HCID 86744613, compound

Product 1

HCID 86744612HCID 86744612, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 220 mg of 2-(octyloxy)-5-[3-(ethoxycarbonyl)benzoyl]benzeneacetic acid, ethyl ester, in 25 ml of ethanol were added 20 mg of sodium borohydride. After 3 hours of stirring, 5 ml of water and 2 ml of hydrochloric acid were added. After stirring for 15 minutes, additional water was added until the solution turned cloudy. The mixture was poured into ethyl acetate and water. The layers were separated, the organic layer was washed three times with water, and the combined water extracts were back extracted with ethyl acetate. The ethyl acetate extracts were combined, dried over magnesium sulfate, and concentrated to dryness providing 190 mg of the desired title product as a colorless oil. NMR.

Workup

  1. stirringAfter stirring for 15 minutes
  2. customThe layers were separated
  3. washthe organic layer was washed three times with water
  4. extractionthe combined water extracts were back extracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-19c4a14d1f8446678142eae82b0972c9
Source dataset
uspto-grants-1993_08
Patent number
US05235064

Reaction notes

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