Sodium Hydroxide → HCID 54498678, compound

HRID 722899Notes

Reaction equation

HRID 722899 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][CH:6]([CH2:11][P:12]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][CH:8]([CH3:10])[CH3:9])C.[OH-].[Na+]>CCO>[CH2:18]([O:17][P:12]([CH2:11][CH:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:5][C:4]([OH:20])=[O:3])([O:14][CH2:15][CH3:16])=[O:13])[CH3:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54362658HCID 54362658, compound

Product 1

HCID 54498678HCID 54498678, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(Diethoxy-phosphorylmethyl)-5-methyl-hexanoic acid ethyl ester (1.0 g, 3.2 mmol) and NaOH (1.8 mL, 2.0 M) are combined in 10 mL of EtOH at 0° C. After 15 minutes, the reaction mixture is warmed to room temperature and stirred overnight. The EtOH is evaporated, and 50 mL of 2.0 M NaOH is added. The solution is extracted with Et2O (2×50 mL), and then acidified to pH=1 with concentrated HCl. The acidic solution is extracted with EtOAc (3×50 mL), and the combined extracts are dried over MgSO4 and evaporated to give 0.65 g (72% yield) of 3-(diethoxy-phosphorylmethyl)-5-methyl-hexanoic acid as an oil. NMR (HI, 400 MHz, CDCl3) δ 0.9 (6H, d); δ 1.3 (8H, m); δ 1.6 (1H, m); δ 1.8 (2H, m); δ 2.3 (1 H, m); δ 2.5 (2H, m); δ 4.1 (4H, m).

Workup

  1. customThe EtOH is evaporated
  2. addition50 mL of 2.0 M NaOH is added
  3. extractionThe solution is extracted with Et2O (2×50 mL)
  4. extractionThe acidic solution is extracted with EtOAc (3×50 mL)
  5. dry with materialthe combined extracts are dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-289a137ae6394d7cb896ca61c18d88b9
Source dataset
uspto-grants-2006_11
Patent number
US07138542B2

Reaction notes

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