Ethyl formate → HCID 178520855, compound

HRID 12569

Reaction equation

HRID 12569 reaction equation
C[CH2:2][O-:3].[Na+].C(OCC)=O.[C:10]1([C:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCO>[OH:17]/[C:16](/[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[C:18](/[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)\[CH:2]=[O:3]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 99482-PhenylacetophenoneHCID 2723922Sodium ethoxide

Product 1

HCID 178520855HCID 178520855, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
2.5 °C

Procedure

To a cooled solution of NaOEt (763 mg, 11.21 mmol) in EtOH (100 ml) was added ethyl formate (0.91 ml, 11.21 mmol) dropwise. The resulting mixture is allowed to stand for 3 hours at 0 to 5° C., and then deoxybenzoin (2 g, 10.19 mmol) was added. The mixture was stirred for 2 hours at 0 to 5° C. and then placed in the refrigerator for 4 days. After the mixture was stirred overnight at room temperature, it was poured into ice-water, and acidified, and extracted with CH2Cl2. The organic layer was washed with brine, and dried over MgSO4 anhydride, and concentrated in vacuo. The residue was purified by column chromatography (10% ethyl acetate in hexane) to give the title compound as a light yellow solid.

Workup

  1. waitplaced in the refrigerator for 4 days
  2. stirringAfter the mixture was stirred overnight at room temperature
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4 anhydride
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8e50eceeef0549698f541ac6041518dd
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Linked notes

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