Hydrochloric Acid → HCID 15106470, compound

HRID 1197100Notes

Reaction equation

HRID 1197100 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]([NH:18][C:19](=[O:37])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:22][CH:21]=2)[CH:6]=1)=[O:4].C(O)C.Cl>C(OCC)(=O)C>[OH:4][CH2:3][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]([NH:18][C:19](=[O:37])[C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:24][CH:25]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 15106469HCID 15106469, compound

Product 1

HCID 15106470HCID 15106470, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Under ice cooling 0.2 g of sodium borohydride was added to a mixture of 2.8 g of ethyl 4-formyl-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate obtained in Reference Example 64 and 30 ml of ethanol. The mixture was stirred for 2 hours and 50 ml of ethyl acetate was added thereto. The mixture was rendered acidic with diluted hydrochloric acid. The ethyl acetate layer was fractionated, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethanol to obtain 2.06 g of ethyl 4-hydroxymethyl-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-d68a7955625d4cb9af62034c236a032a
Source dataset
uspto-grants-1992_05
Patent number
US05116853

Reaction notes

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