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Hydrochloric Acid → 4-acetyl-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7883
Notes
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Reaction equation

HRID 7883 reaction equation
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]([O:21]CC)=[CH2:20])=[C:13]1[C:12]1[C:7](=[C:8]([Cl:26])[C:9]([O:24][CH3:25])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].Cl>C(O)C.O>[C:19]([C:14]1[C:15](=[O:18])[CH2:16][CH2:17][C:5]2([CH2:1][CH2:2][CH2:3][CH3:4])[C:13]=1[C:12]1[C:7](=[C:8]([Cl:26])[C:9]([O:24][CH3:25])=[CH:10][CH:11]=1)[CH2:6]2)(=[O:21])[CH3:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 219909099a-butyl-8-chloro-4-(1-ethoxyvinyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 219908794-acetyl-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The product from step 1 in ethanol (1.0 mL), water (0.2 mL) and aqueous 2N HCl (0.2 mL) was stirred and heated in an oil bath at 80° C. for 40 minutes. After cooling, the mixture was partitioned between EtOAc (20 mL) and water (20 mL). The organic phase was washed with brine (20 mL), dried over MgSO4, filtered, and evaporated under vacuum to provide 4-acetyl-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (54 mg) as an oil.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between EtOAc (20 mL) and water (20 mL)
  3. washThe organic phase was washed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-194006f950674b50a93e6edc19549752
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087599B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes