Sodium → HCID 20156956, compound

HRID 986644Notes

Reaction equation

HRID 986644 reaction equation
[Na].[CH2:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)[CH3:3].Cl[CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[C:28]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:27]=1>O1CCOCC1>[CH2:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[C:28]([O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:27]=2)([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:10]=1)[CH3:3]

Participants

5

Reactant 3

HCID 5360545Sodium2×HCID 15557860Diethyl (4-ethoxyphenyl)propanedioateHCID 20156955HCID 20156955, compound

Product 1

HCID 20156956HCID 20156956, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium (2.18 g, 35 mmol) was added to diethyl 4-ethoxyphenylmalonate (26.6 g, 95 mmol) dissolved in dioxane (100 ml) and refluxed until the sodium had dissolved. Chloromethyl(4-fluoro-3-phenoxybenzyl)ether (25.4 g, 95 mmol) was added, dropwise, at 40°-50° C. and then heated under reflux for 3 hours. The mixture was added to ice-water, extracted three times with ether, the extracts washed with water, dried over magnesium sulphate and evaporated. After chromatography on silica-gel, using toluene as the eluent, there was obtained 25.3 g of diethyl 2-(4-ethoxyphenyl)-2-(4-fluoro-3-phenoxybenzyloxymethyl)malonate (52% of theory). This was then reduced in a similar manner to Example 1 using lithium aluminium hydride to give crude 2-(4-ethoxyphenyl)-2-(4-fluoro-3-phenoxybenzyloxymethyl)propane-1,3-diol.

Workup

  1. dissolutionhad dissolved
  2. temperaturedropwise, at 40°-50° C. and then heated
  3. temperatureunder reflux for 3 hours
  4. extractionextracted three times with ether
  5. washthe extracts washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-4eb2b335617b417eb67786e91e12bdd6
Source dataset
uspto-grants-1987_12
Patent number
US04714710

Reaction notes

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