Acetic Acid → HCID 21990921, compound

HRID 7832Notes

Reaction equation

HRID 7832 reaction equation
[CH2:1]([C:5]1([CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=O)[CH2:2][CH2:3][CH3:4].N1CCCC1.C(O)(=O)C>>[CH2:1]([C:5]12[CH2:17][CH2:18][C:19](=[O:21])[CH:20]=[C:6]1[C:7]1[C:12](=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=1)[CH2:13]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 219908542-Butyl-5-methoxy-2-(3-oxo-butyl)-1-indanone

Product 1

HCID 21990921HCID 21990921, compound

Conditions

Temperature
60 °C

Procedure

The solution from step 2 was treated with pyrrolidine (6.9 mL, 82 mmol) and acetic acid (4.7 mL, 82 mmol), placed under a nitrogen atmosphere, and stirred with heating in a 60° C. bath for 22 hours. After cooling to room temperature, the reaction mixture was partitioned between EtOAc (500 mL) and water (500 mL). The EtOAc phase was washed with 0.8N HCl (500 mL), water (500 mL), 5% NaHCO3 (500 mL), and brine (200 mL), dried with MgSO4, filtered, and evaporated under vacuum to a brown oil (22.8 g). This material was purified by column chromatography on EM silica gel 60 (230-400 mesh, 684 g), using 5% EtOAc in CH2Cl2 as eluting solvent, to afford 9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (11.2 g) as a solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between EtOAc (500 mL) and water (500 mL)
  3. washThe EtOAc phase was washed with 0.8N HCl (500 mL), water (500 mL), 5% NaHCO3 (500 mL), and brine (200 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum to a brown oil (22.8 g)
  7. customThis material was purified by column chromatography on EM silica gel 60 (230-400 mesh, 684 g)
  8. washas eluting solvent

Sources & evidence

ORD record
ord-6eb19596dc4f425b98b352cad4d4b671
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Reaction notes

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