Sodium Hydroxide → HCID 57084727, compound

HRID 565231Notes

Reaction equation

HRID 565231 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@H:15]([OH:17])[CH3:16])[C:11]([O:13]C)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.CO>[C:1]1([CH2:7][CH2:8][CH2:9][C@H:10]([C@H:15]([OH:17])[CH3:16])[C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57288795HCID 57288795, compound

Product 1

HCID 57084727HCID 57084727, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of methyl (2R,3R)-2-(3-phenyl-1-propyl)-3-hydroxybutanoate (42.2 g, 179.5 mmol) in THF-methanol (3:1, 535 mL) is added 2 M aqueous sodium hydroxide solution (135 mL, 269.3 mmol). The solution is stirred at 23° C. for 20 h, then concentrated and extracted with hexanes (100 mL). The aqueous layer is acidified to pH=3 with saturated aqueous sodium bisulfate and is extracted with two 500 mL portions of ethyl acetate. 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-hydroxybutanoic acid as an oil (33.0 g, 83% yield).

Workup

  1. concentrationconcentrated
  2. extractionextracted with hexanes (100 mL)
  3. extractionis extracted with two 500 mL portions of ethyl acetate
  4. dry with materialThe combined organic layers are dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e64912cc00444a49fdbcb2d353d6593
Source dataset
uspto-grants-2001_01
Patent number
US06172064B2

Reaction notes

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