Sodium Hydroxide → HCID 57197129, compound

HRID 2269358Notes

Reaction equation

HRID 2269358 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@H:16]([OH:20])[CH2:17][CH2:18][CH3:19])[C:11]([O:13]CC)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].S(=O)(=O)(O)[O-].[Na+]>C1COCC1.C(O)C>[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@H:16]([OH:20])[CH2:17][CH2:18][CH3:19])[C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 57062265HCID 57062265, compound

Product 1

HCID 57197129HCID 57197129, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of ethyl (2R,3R)-2-(3-phenyl-1-propyl)-3-hydroxyhexanoate (1.70 g, 6.12 mmol) in THF-ethanol (2:1, 18 mL) is added 1 N aqueous sodium hydroxide solution (6.7 mL, 6.7 mmol). The solution is stirred at 23° C. for 20 h and is acidified to pH 3 with saturated aqueous sodium bisulfate and is extracted with two 50-mL portions of EtOAc. The combined organic layers are dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide (2R,3R)-2-(3-phenyl-1-propyl)-3-hydroxyhexanoic acid as an oil (1.53 g, 100% yield).

Workup

  1. extractionis extracted with two 50-mL portions of EtOAc
  2. dry with materialThe combined organic layers are dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e2c699746004f1fb937501b1dd9851c
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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