Tetrahydrofuran → HCID 18459226, compound

HRID 2304989Notes

Reaction equation

HRID 2304989 reaction equation
C([O:3][C:4]([C:6]([CH3:33])([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:21][CH:20]=1)[CH2:7][CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[O:5])C.[OH-].[Na+].O1CCCC1>CO.C(OCC)(=O)C>[C:4]([C:6]([CH3:33])([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:21][CH:20]=1)[CH2:7][CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([OH:5])=[O:3]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18459230HCID 18459230, compound

Product 1

HCID 18459226HCID 18459226, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (±)-diethyl 3-ethoxycarbonyl-3-methyl-5-(4-(octyl)phenyl)pentylphosphonate (0.211 g, 0.437 mmol) in methanol (2 ml) was added 1N aqueous sodium hydroxide (1.3 ml, 1.3 mol). Tetrahydrofuran was added as necessary to keep the substrate in solution. The reaction was heated to 50° C. for 16 h then warmed to 70° and stirred at this temperature for 20 h. The reaction was diluted with ethyl acetate (30 ml) and washed with 2N aq HCl (20 ml), saturated aqueous sodium chloride (20 ml), dried over magnesium sulfate and concentrated to give a colorless oil (0.164 g): MS m/e 455.2 (M+).

Workup

  1. temperaturethen warmed to 70°
  2. washwashed with 2N aq HCl (20 ml), saturated aqueous sodium chloride (20 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6d5701835c8d418f9b3660a560637cd3
Source dataset
uspto-grants-2002_08
Patent number
US06437165B1

Reaction notes

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