Hydrochloric Acid → HCID 58604047, compound

HRID 2113671Notes

Reaction equation

C(OC([C:6]1([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([F:19])=[C:11]([O:17][CH3:18])[C:12]=2[Cl:16])[C:7]1=[O:20])=O)C.Cl>CC(O)=O>[CH2:21]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([F:19])=[C:11]([O:17][CH3:18])[C:12]=2[Cl:16])[C:7]1=[O:20])[CH2:22][CH2:23][CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

2-butyl-5-chloro-7-fluoro-6-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester (263 mg, 0.74 mmol) was dissolved in AcOH (6 mL) then treated with 6N HCl (6 mL). This solution was heated with stirring at 80° C. for 75 minutes, then at 100° C. for 2 hours. After cooling to room temperature the mixture was partitioned between EtOAc/5% NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and evaporated under vacuum. Two successive purifications of the crude product by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7.5 cm) silica gel columns, eluting with EtOAc/hexane yielded 2-butyl-5-chloro-7-fluoro-6-methoxy-3,4-dihydro-2H-naphthalen-1-one and recovered starting material.

Workup

temperatureThis solution was heated
waitat 100° C. for 2 hours
temperatureAfter cooling to room temperature the mixture
customwas partitioned between EtOAc/5% NaHCO3
washThe organic phase was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated under vacuum
washTwo successive purifications of the crude product by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7.5 cm) silica gel columns, eluting with EtOAc/hexane

Sources & evidence

ORD record: ord-a451bcdfb27845d9852a290b079be9d9
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432284B2

Reaction notes

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