Hydrochloric Acid → HCID 20069042, compound

HRID 982098Notes

Reaction equation

HRID 982098 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][C:9]2=[O:15].[CH3:22]I.Cl>CCCCCC.CS(C)=O>[OH:3][C:4]1[C:13]([O:14][CH3:22])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][C:9]2=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20069025HCID 20069025, compound

Product 1

HCID 20069042HCID 20069042, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Procedure

A 60% dispersion of sodium hydride in mineral oil (0.39 g, 9.8 mmol) was washed with hexane and the hexane was decanted. DMSO (15 mL) was added to the sodium hydride and the resultant suspension was stirred vigorously. To the suspension was added a solution of 2.5 g (9.8 mmol) of 5,6-dihydroxy-3-phenyl-1,2,3,4-tetrahydro-1-naphthalenone, from Step 1, in 10 mL of DMSO. The mixture was stirred at ambient temperature for 80 min and 0.61 mL (9.8 mmol) of methyl iodide was added in one portion. The reaction mixture was stirred at ambient temperature overnight and then made acidic with 5% aqueous hydrochloric acid solution. The mixture was stirred for 30 min and then filtered. The filter cake was dissolved in 20% ethyl acetate in hexane and chromatographed on a silica gel column eluted with 20% ethyl acetate in hexane and 50% ethyl acetate in hexane to give a brown solid. The solid was crystallized from ethyl acetate to give 1.13 g (43% yield) of the title compound as white crystals.

Workup

  1. customthe hexane was decanted
  2. additionDMSO (15 mL) was added to the sodium hydride
  3. stirringThe mixture was stirred at ambient temperature for 80 min
  4. stirringThe reaction mixture was stirred at ambient temperature overnight
  5. stirringThe mixture was stirred for 30 min
  6. filtrationfiltered
  7. dissolutionThe filter cake was dissolved in 20% ethyl acetate in hexane
  8. customchromatographed on a silica gel column
  9. washeluted with 20% ethyl acetate in hexane and 50% ethyl acetate in hexane
  10. customto give a brown solid
  11. customThe solid was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-472c4de6fd6f41009dc482e42791a4a4
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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