Acetic Acid → HCID 58550541, compound

HRID 1891005Notes

Reaction equation

HRID 1891005 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:16])[CH3:15].[CH2:17]([O:19][C:20](=O)[O:21]CC)[CH3:18].[H-].[Na+].CC(O)=O>C1(C)C=CC=CC=1.O>[CH2:17]([O:19][C:20](=[O:21])[CH2:15][C:14](=[O:16])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][CH2:6][CH:2]1[CH2:3][CH2:4][CH2:5][O:1]1)[CH3:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 24697475HCID 24697475, compound

Product 1

HCID 58550541HCID 58550541, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A mixture of 1-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-ethanone (2.22 g, 0.01 mol) and diethylcarbonat (10 mL, 0.083 mol) in anhydrous toluene (20 mL) was added dropwise to a suspension NaH (1.0 g, 0.025 mol) in anhydrous toluene (20 mL). After addition, the mixture refluxed for 2 h, cooled and poured slowly into a solution AcOH (3 mL) and water (50 mL). After separated the organic layer, the aqueous layer was extracted with ethyl acetate (2×50 mL). Organic layers were combined, washed with water (20 mL), then dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash chromatography on silica gel (eluent hexane-ethylacetate, 1:5) to obtain 1.85 g (64%) 3-oxo-3-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-propionic acid ethyl ester as yellow oil.

Workup

  1. additionAfter addition
  2. temperaturethe mixture refluxed for 2 h
  3. temperaturecooled
  4. customAfter separated the organic layer
  5. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  6. washwashed with water (20 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel (eluent hexane-ethylacetate, 1:5)

Sources & evidence

ORD record
ord-5d0bfafedf7c4f7d9acb9e4c3f1e042c
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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