Sodium Hydroxide → HCID 85863446, compound

HRID 970061Notes

Reaction equation

HRID 970061 reaction equation
[C:1]([CH:6]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:7][CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([O:3]CC)=[O:2].[OH-].[Na+]>CO.CCOC(C)=O>[C:1]([CH:6]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:7][CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 85863443HCID 85863443, compound

Product 1

HCID 85863446HCID 85863446, compoundYield 109.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution 0.61 g (1.44 mmol) of (±)-diethyl 3-(carboethoxy)pentadecyl phosphonate (from Example 27, Step A) in 10 mL of MeOH was treated with 4.3 mL of 1 N NaOH. The resulting mixture was stirred at rt for 2 h then heated to 50° C. for 16 h. The reaction was diluted with 75 mL of EtOAc, washed with 50 mL of 2 N HCl, 50 mL of sat'd NaCl, dried and concentrated to give 0.62 g of the title compound: ESI-MS 393.1 (M+H).

Workup

  1. temperaturethen heated to 50° C. for 16 h
  2. washwashed with 50 mL of 2 N HCl, 50 mL of sat'd NaCl
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9bc09aedda1c4a5888209aacc12f6e47
Source dataset
uspto-grants-2007_12
Patent number
US07309721B2

Reaction notes

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