Acetic Anhydride → HCID 67197066, compound

HRID 598764Notes

Reaction equation

HRID 598764 reaction equation
[CH2:1]1[CH2:6][C@@H:5]2[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C@H:4]2[CH2:3][CH2:2]1.[C:12](OC(=O)C)(=[O:14])[CH3:13].[Cl-].[NH4+]>>[C:12]([CH:9]1[CH2:8][CH2:7][CH:5]2[CH:4]([CH2:3][CH2:2][CH2:1][CH2:6]2)[C:10]1=[O:11])(=[O:14])[CH3:13]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 89486trans-Bicyclo(4.4.0)decan-1-one

Product 1

HCID 67197066HCID 67197066, compoundYield 19.8%

Procedure

Boron trifluoride-acetic acid complex (5.2 mL, 37.5 mmol) was cooled to 0° C. trans-1-Decalone (3.82 g, 25 mmol) in acetic anhydride (4.7 mL, 50 mmol) was added, and the reaction was stirred at room temperature for 3.5 hours. Saturated ammonium chloride solution (95 mL) was added, and the mixture was heated to 80° C. for 45 minutes. After cooling to room temperature, the mixture was extracted with ethyl acetate. The extracts were dried over MgSO4 and concentrated. SiO2 chromatography with 10-40% ethyl acetate/hexanes gave 0.96 g of the desired product.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated to 80° C. for 45 minutes
  3. temperatureAfter cooling to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extracts were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f9ce182ad99949fca236c14ad3bce6f7
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

Loading…