Hydrochloric Acid → HCID 59478800, compound

HRID 1747068Notes

Reaction equation

HRID 1747068 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C@@H:7]([CH3:15])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:2].[BH4-].[Na+].O.Cl>CO.C(OCC)(=O)C>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C@@H:7]([CH3:15])[C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 86645200tert-butyl(2S)-2-(3-formylphenoxy)propanoate

Product 1

HCID 59478800HCID 59478800, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.48 g of tert-butyl(2S)-2-(3-formylphenoxy)propanoate in methanol (30 mL) was added 0.48 g of sodium borohydride under ice-cooling, followed by stirring for 1 hour. The reaction solution was diluted with ethyl acetate, added with water, neutralized with 1 M hydrochloric acid, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 1.38 g of tert-butyl(2S)-2-[3-(hydroxymethyl)phenoxy]propanoate as a colorless oily substance.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27673484b39c4982972e89a2e2dd73c9
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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