Water → HCID 69306558, compound

HRID 1393863Notes

Reaction equation

HRID 1393863 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([OH:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24][O:25][CH2:26][CH2:27][O:28][CH2:29]Cl.O>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([O:19][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 69307856HCID 69307856, compound

Product 1

HCID 69306558HCID 69306558, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-{4-[(4-fluorobenzyl)oxy]phenyl}-2-hydroxyacetate (0.507 g, 1.75 mmol) was dissolved in tetrahydrofuran (9 ml), and sodium hydride (0.09 g, 2.27 mmol) was added thereto while being cooled with ice. The mixture was stirred for 30 minutes at room temperature, and 2-methoxyethoxymethylchloride (0.26 ml, 2.27 mmol) was added thereto while being cooled with ice. After being stirred for 62 hours at room temperature, the mixture, with water added thereto, was extracted with ethyl acetate. The organic layer was dried over MgSO4, and then the solvent was evaporated out. The obtained residue was purified by silica gel column chromatography (30% ethyl acetate/hexane), to give methyl 2-{4-[(4-fluorobenzyl)oxy]phenyl}-2-[(2-methoxyethoxy)methoxy]acetate (0.421 g, 64%).

Workup

  1. temperaturewhile being cooled with ice
  2. temperaturewhile being cooled with ice
  3. stirringAfter being stirred for 62 hours at room temperature
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent was evaporated out
  7. customThe obtained residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-81e242eb6daf4ea4b4c664d7a1a62ada
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

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