Ethyl formate → HCID 117720313, compound

HRID 530248Notes

Reaction equation

HRID 530248 reaction equation
[CH3:1][O-].[Na+].[C:4]1(=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C([O:14][CH2:15][CH3:16])=O>C1(C)C=CC=CC=1>[CH3:1][C:6]1([CH3:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:4]/[C:16]/1=[CH:15]\[OH:14]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 10400CycloheptanoneHCID 10942334Sodium Methoxide

Product 1

HCID 117720313HCID 117720313, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred mixture of powdered sodium methoxide (3.0 g, 56.16 mmol) in toluene (90 mL) at 0° C. was added cycloheptanone (6.0 g, 53.49 mmol) and ethyl formate (7.92 g, 106.98 mmol). The mixture was warmed to room temperature and stirred overnight. Ice water (70 mL) was added and the organic phase separated. The organic phase was washed by 5% aqueous sodium hydroxide (30 mL×2) and the combined aqueous phase was acidified to pH=3 with 2 N hydrochloric acid and then extracted with ethyl acetate (120 mL×3). The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=80/1) to afford the title compound as a colorless oil (4.26 g, Yield: 57%). Rf=0.6 (20:1 petroleum ether/ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 14.68 (d, J=9.2 Hz, 1H), 7.63 (d, J=9.2 Hz, 1H), 2.55-2.52 (m, 2H), 2.26-2.24 (m, 2H), 1.76-1.58 (m, 6H) ppm.

Workup

  1. customthe organic phase separated
  2. washThe organic phase was washed by 5% aqueous sodium hydroxide (30 mL×2)
  3. extractionextracted with ethyl acetate (120 mL×3)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=80/1)

Sources & evidence

ORD record
ord-11f946d6e5b44b958ad8dfc293303143
Source dataset
uspto-grants-2016_05
Patent number
US09353063B2

Reaction notes

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