Methanol → HCID 54172140, compound

HRID 1898954Notes

Reaction equation

HRID 1898954 reaction equation
C(Cl)(=O)C.CO.[C:7]([O:11][CH3:12])(=[O:10])[CH2:8][SH:9].[CH:13]1[CH:27]=[C:26]2[C:16]([CH:17](O)[C:18]3[C:23]([CH:24]=[CH:25]2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:14]=1>C(OCC)(=O)C>[CH:22]1[C:23]2[CH:24]=[CH:25][C:26]3[CH:27]=[CH:13][CH:14]=[CH:15][C:16]=3[CH:17]([S:9][CH2:8][C:7]([O:11][CH3:12])=[O:10])[C:18]=2[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 16907Methyl ThioglycolateHCID 82577Dibenzosuberenol

Product 1

HCID 54172140HCID 54172140, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetyl chloride (171 μL, 2.4 mmol) is carefully added to 8 mL of dry methanol and the solution is stirred for 15 minutes. Methyl thioglycolate (257 μL, 2.9mmol) and dibenzosuberenol (Aldrich) (0.50 g, 2.4 mmol) are added, and the reaction is stirred for 5 minutes. The reaction is diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate, water, then brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil is chromatographed on silica gel eluting with ethyl acetate:toluene:hexane (3:27:70) to give 0.62 g (87%) of methyl (5H-dibenzo[a,d]cyclohepten-5-yl-thio)acetate: melting point 74°-76° C.

Workup

  1. stirringthe reaction is stirred for 5 minutes
  2. washwashed with saturated aqueous sodium bicarbonate, water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting oil is chromatographed on silica gel eluting with ethyl acetate:toluene:hexane (3:27:70)

Sources & evidence

ORD record
ord-bbb5f3394b3b45bdb8b68b9b69dfb119
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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