Diethyl Oxalate → HCID 178473091, compound

HRID 915427Notes

Reaction equation

HRID 915427 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[C:15](OCC)(=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].[Na]>C(O)C>[CH2:19]([O:18][C:16](=[O:17])/[C:15](/[OH:21])=[CH:11]/[C:10](=[O:12])[C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:9][CH:8]=1)[CH3:20]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 5228211-(4-(Trifluoromethoxy)phenyl)ethan-1-oneHCID 5360545Sodium

Product 1

HCID 178473091HCID 178473091, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 1-(4-trifluoromethoxy-phenyl)-ethanone (5 g, 24 mmol) and diethyl oxalate (3.25 ml, 24 mmol) in ethanol (5 ml) was added within 20 min to an ice cooled solution of metallic sodium (552 mg, 24 mmol) in ethanol (15 ml) under an argon atmosphere. The cooling bath was removed and the reaction stirred 30 min after reaching ambient temperature. After standing 14 h, the precipitated yellow solid was filtered. The solid was partitioned between 1 M HCl/ice water 1/1 and tert butyl methyl ether. The aqueous layer was extracted two times with tert butyl methyl ether, the combined extracts were washed with brine/ice water 1/1 and dried over sodium sulfate. Evaporation of the solid gave 7.2 g (23.8 mmol, 99%) of the title compound as orange crystals.

Workup

  1. customThe cooling bath was removed
  2. customafter reaching ambient temperature
  3. waitAfter standing 14 h
  4. filtrationthe precipitated yellow solid was filtered
  5. customThe solid was partitioned between 1 M HCl/ice water 1/1 and tert butyl methyl ether
  6. extractionThe aqueous layer was extracted two times with tert butyl methyl ether
  7. washthe combined extracts were washed with brine/ice water 1/1
  8. dry with materialdried over sodium sulfate
  9. customEvaporation of the solid

Sources & evidence

ORD record
ord-06f83d3955184b1e90bb6762be790bd6
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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