Potassium Carbonate → HCID 22826055, compound

HRID 1903820Notes

Reaction equation

HRID 1903820 reaction equation
[CH3:1][C:2]1([CH3:23])[O:7][C:6]2[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:10]=[C:11]([OH:12])[C:5]=2[C@@H:4]2[CH:18]=[C:19]([CH3:22])[CH2:20][CH2:21][C@@H:3]12.Br[CH2:25][CH2:26][CH2:27][C:28]([O:30]CC)=[O:29].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:23][C:2]1([CH3:1])[O:7][C:6]2[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:10]=[C:11]([O:12][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:5]=2[C@@H:4]2[CH:18]=[C:19]([CH3:22])[CH2:20][CH2:21][C@@H:3]12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16078TetrahydrocannabinolHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 22826055HCID 22826055, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1.73 g (5.50 mmol) of (6aR-trans)-6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol, 10 ml of dimethylsulfoxide, 3 ml of ethyl 4-bromobutyrate and 1.73 g of potassium carbonate was degassed and then heated under reflux under argon over night. The reaction was cooled, diluted with 250 ml of water and extracted with ether. The extracts were passed over a column of silica gel, and the fractions containing the intermediate ester were combined and concentrated under vacuum. The residue was dissolved in 100 ml of methanol, the solution was heated to boiling and 20 ml of water, followed by 2.2 g of sodium carbonate, was added. The mixture was heated under reflux for 3 hrs. The methanol was evaporated under vacuum, and the aqueous residue was acidified with hydrochloric acid and extracted with dichloromethane. The extracts were concentrated, and the residue was dissolved in hexane and adsorbed onto silica gel. Elution with 15% ethyl acetate in benzene, followed by evaporation, gave 1.70 g (77%) of (6aR-trans)-4-[(6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid as a colorless oil: ir (CHCl3) 1710 cm-1 ; uv max (C2H5OH) 225 nm (infl) (ε17,830), 274 (1090), and 282 (1120); nmr (CDCl3) δ11.3 (br, CO2H), 6.29 and 6.20 (two sharp d, H-2 and H-4), 5.41 (m, H-8), 4.01 (t, OCH2C), 3.18 (m, H-10a), 2.59 (t, ArCH2C), 2.48 (t, CCH2CO), 1.69 (s, 9-CH3), 1.34 and 1.06 (two s, 6,6-diCH3), and 0.87 (t, ω-CH3); mass mol wt 400; [α]D25° -195.3° (c 1.104, CHCl3).

Workup

  1. customwas degassed
  2. temperatureheated
  3. temperatureunder reflux under argon over night
  4. temperatureThe reaction was cooled
  5. additiondiluted with 250 ml of water
  6. extractionextracted with ether
  7. additionthe fractions containing the intermediate ester
  8. concentrationconcentrated under vacuum
  9. dissolutionThe residue was dissolved in 100 ml of methanol
  10. temperaturethe solution was heated
  11. additionwas added
  12. temperatureThe mixture was heated
  13. temperatureunder reflux for 3 hrs
  14. customThe methanol was evaporated under vacuum
  15. extractionextracted with dichloromethane
  16. concentrationThe extracts were concentrated
  17. dissolutionthe residue was dissolved in hexane
  18. washElution with 15% ethyl acetate in benzene
  19. customfollowed by evaporation

Sources & evidence

ORD record
ord-ba9836188f89481bb3a87f126f207513
Source dataset
uspto-grants-1984_03
Patent number
US04438207

Reaction notes

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