Ethanol → HCID 178473078, compound

HRID 1426317Notes

Reaction equation

HRID 1426317 reaction equation
C(O)C.[H-].[Na+].[CH:6]1([C:10](=[O:12])[CH3:11])[CH2:9][CH2:8][CH2:7]1.[C:13](OCC)(=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].S(=O)(=O)(O)O.O>>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[O:19])[CH:11]=[C:10]([CH:6]1[CH2:9][CH2:8][CH2:7]1)[OH:12])[CH3:18]

Participants

7

Reactant 6

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 763981-Cyclobutylethan-1-one

Product 1

HCID 178473078HCID 178473078, compound

Procedure

Ethanol (4.39 mL, 75.2 mmol) was added dropwise to a suspension of sodium hydride (0.607 g, 15.2 mmol, 60% in mineral oil) in a flask that was held in an ice bath. Ten minutes after complete addition, a mixture of 1-cyclobutylethanone (1.5 mL, 14 mmol, Aldrich) and diethyl oxalate (2.01 g, 13.8 mmol, Aldrich) was added dropwise. After stirring overnight, 4.0M sulfuric acid in water (0.00759 L, 30.4 mmol) was added. The product was extracted into diethyl ether. The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The material was used without further purification in Step B.

Workup

  1. customwas held in an ice bath
  2. additionTen minutes after complete addition
  3. additionwas added dropwise
  4. extractionThe product was extracted into diethyl ether
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe material was used without further purification in Step B

Sources & evidence

ORD record
ord-dae224ca773c47b6a4f102e35e047a94
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

Loading…