Hydrochloric Acid → HCID 20298321, compound

HRID 1389183Notes

Reaction equation

HRID 1389183 reaction equation
C[O:2][C:3]1[CH:8]=C(CNCCCNCCCCNCCCN)C=[CH:5][C:4]=1O.[OH:25][C:26]1[CH:35]=[C:34]([O:36][CH:37]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH3:38])[CH:33]=[C:32]2[C:27]=1[C:28](=O)[C:29](=CO)[C:30]([CH3:45])([CH3:44])[O:31]2.CC(C=C)=O.[OH-].[K+].Cl>CO.CCOCC.C(O)C.C(N(CC)CC)C>[OH:31][C:32]1[C:27]2[C:28]3=[CH:8][C:3](=[O:2])[CH2:4][CH2:5][CH:29]3[C:30]([CH3:45])([CH3:44])[O:25][C:26]=2[CH:35]=[C:34]([O:36][CH:37]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH3:38])[CH:33]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6570Methyl vinyl ketoneHCID 14797Potassium HydroxideHCID 131711452HCID 131711452, compound

Product 1

HCID 20298321HCID 20298321, compoundYield 42.3%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of dl-5-hydroxy-3-hydroxymethylene-2,2-dimethyl-7-(2-heptyloxy)-4-chromanone (5.17 g., 15.4 mM) and methylvinyl ketone (2.27 ml., 27.9 mM) in methanol (23 ml.) is added triethylamine (0.54 ml.). The reaction is stirred for 16 hours at room temperature and then diluted with ether (250 ml.). The resulting ether solution is extracted with 10% sodium carbonate (6×30 ml.), dried over sodium sulfate, and concentrated under vacuum to yield 6.11 g. of an oil. The residue is refluxed with ethanol (45 ml.) and 2 N potassium hydroxide (45 ml.) for 16 hours. Thereafter, the reaction solution is cooled, acidified with 6 N hydrochloric acid and extracted with dichloromethane (3×100 ml.). The organic phase is dried over sodium sulfate and evaporated to yield 6.3 g. of a dark solid. The solid is triturated in hot ether to yield 1.00 g. of the title compound, m.p. 185°-189° C.; 1.26 g. of further material is obtained via silica gel chromatography of the mother liquor. The total yield is 42.3%.

Workup

  1. extractionThe resulting ether solution is extracted with 10% sodium carbonate (6×30 ml.)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customto yield 6.11 g
  5. temperatureThereafter, the reaction solution is cooled
  6. extractionextracted with dichloromethane (3×100 ml.)
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. customevaporated
  9. customto yield 6.3 g
  10. customThe solid is triturated in hot ether
  11. customto yield 1.00 g

Sources & evidence

ORD record
ord-43e4027fa101467085f6d7d8a6337138
Source dataset
uspto-grants-1981_01
Patent number
US04243674

Reaction notes

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