N,N-Diethylethanamine trihydrofluoride → Cannabidiol glycolate

HRID 2067149Notes

Reaction equation

[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([OH:23])[C:9]([C@H:13]2[C@H:18]([C:19]([CH3:21])=[CH2:20])[CH2:17][CH2:16][C:15]([CH3:22])=[CH:14]2)=[C:10]([OH:12])[CH:11]=1.[Si]([O:31][CH2:32][C:33]([O-:35])=[O:34])(C(C)(C)C)(C)C.F.F.F.C(N(CC)CC)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>ClCCl>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([OH:12])[C:9]([C@H:13]2[C@H:18]([C:19]([CH3:21])=[CH2:20])[CH2:17][CH2:16][C:15]([CH3:22])=[CH:14]2)=[C:8]([OH:23])[CH:7]=1.[C:33]([O-:35])(=[O:34])[CH2:32][OH:31]

Participants

Conditions

Temperature: -15 °C

Procedure

Cannabidiol (t-butyldimethylsilyloxy)acetate (80 mg) was dissolved in dry dichloromethane (0.25 mL), cooled to −15° C. and treated with 0.25 mL of cold 2 M solution of triethylamine trihydrofluoride in dichloromethane. The reaction mixture was left at 5° C. for 65 h. The mixture was poured to an excess of aqueous saturated sodium bicarbonate/ethyl acetate cooled to 0° C. with vigorous stirring. Aqueous layer was extracted twice with ethyl acetate, the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on silica gel with hexane-ethyl acetate (gradient 10:1, 4:1, 3:1) to afford 58 mg (95%) of cannabidiol glycolate (ALL00149) as an oil.

Workup

temperaturecooled to 0° C. with vigorous stirring
extractionAqueous layer was extracted twice with ethyl acetate
washthe combined organic extracts were washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was chromatographed on silica gel with hexane-ethyl acetate (gradient 10:1, 4:1, 3:1)

Sources & evidence

ORD record: ord-a5ba2d88e6ee4151a3385759ff426bdd
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293786B2

Reaction notes

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