Dimethyl Sulfoxide → Ethyl 3-benzyloxy-5-fluorophenylacetate

HRID 1108065Notes

Reaction equation

HRID 1108065 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16](C(OCC)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)CC(OCC)=O.CS(C)=O.[Li+].[Cl-]>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7761Diethyl MalonateHCID 433294Lithium ChlorideHCID 54386911Diethyl 3-benzyloxy-5-fluorophenylmalonate

Product 1

HCID 18786372Ethyl 3-benzyloxy-5-fluorophenylacetateYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The above mixture of a mixture of diethyl 3-benzyloxy-5-fluorophenylmalonate and diethyl malonate (ca. 1:1.2, 1.0 g), DMSO (10 ml), water (0.1 ml), and LiCl (346 mg) were placed in a 50 ml round-bottom flask equipped with a magnetic stirrer and fitted with a condenser. The mixture was heated at reflux for 5 hr. The mixture was poured into water (50 ml) and the whole extracted with n-hexane (2×50 ml). The combined organic extracts were washed with water (50 ml), brine (50 ml) and dried over Na2SO4. Removal of solvent gave 283 mg (57%) of ethyl 3-benzyloxy-5-fluorophenylacetate as a yellow oil.

Workup

  1. customwere placed in a 50 ml round-bottom flask
  2. customequipped with a magnetic stirrer
  3. customfitted with a condenser
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 5 hr
  6. extractionthe whole extracted with n-hexane (2×50 ml)
  7. washThe combined organic extracts were washed with water (50 ml), brine (50 ml)
  8. dry with materialdried over Na2SO4
  9. customRemoval of solvent

Sources & evidence

ORD record
ord-1216f0578c034012b7ce6ba4935ae3f7
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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