Hydrochloric Acid → HCID 60003050, compound

HRID 2180472Notes

Reaction equation

[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:26][CH3:27])=[C:10](/[C:13](/[CH3:25])=[CH:14]\[CH:15]=[CH:16]\[C:17](\[CH3:24])=[CH:18]\[C:19]([O:21]CC)=[O:20])[CH:11]=2)[O:6][C:5]([CH3:29])([CH3:28])[CH:4]=1)[CH3:2].[OH-].[Na+].Cl>C(O)C.C1COCC1>[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:26][CH3:27])=[C:10](/[C:13](/[CH3:25])=[CH:14]\[CH:15]=[CH:16]\[C:17](\[CH3:24])=[CH:18]\[C:19]([OH:21])=[O:20])[CH:11]=2)[O:6][C:5]([CH3:28])([CH3:29])[CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 7-(4-ethyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)3-methyl-octa-2E,4E,6Z-trienoate (Compound 32, 50 mg, 0.13 mmol) in ethanol (5 mL) and THF (2 mL) was added 1M NaOH (1.0 mL, 1.0 mmol). The mixture was heated to 60° C. for 5 h and was cooled to room temperature, acidified with 1M HCl, and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 30% ethyl acetate in hexanes) followed by recrystallization from acetonitrile to give the title compound as a light yellow solid.

Workup

temperaturewas cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography (silica gel, 30% ethyl acetate in hexanes)
customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record: ord-b35f1b50602c4a1abe071d44bc811c1b
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887896B1

Reaction notes

Loading…