Acetyl chloride → HCID 15157280, compound

HRID 2051431Notes

Reaction equation

HRID 2051431 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.C(Cl)(=[O:10])C.Cl.[OH:13][C:14]1[C:15]([CH:30]([CH3:33])[CH:31]=[CH2:32])=[CH:16][C:17]([CH3:29])=[C:18]2[C:26]=1C(NC)C1[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]1>C(Cl)(Cl)Cl.O>[OH:13][C:14]1[C:15]([CH:30]([CH3:33])[CH:31]=[CH2:32])=[CH:16][C:17]([CH3:29])=[C:18]2[C:26]=1[CH:4]([N:3]([CH3:1])[C:6](=[O:10])[CH3:7])[CH:5]1[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19833499HCID 19833499, compound

Product 1

HCID 15157280HCID 15157280, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

5.4 Milliliters of triethylamine and then 1.43 ml of acetyl chloride were added dropwise to a solution of a chloroform solution containing 5.0 g of 8-hydroxy-5-methyl-9-methylamino-7-(1-methyl-2-propenyl)-1,2,3,4,4a,9a-hexahydrofluorene hydrochloride with stirring under ice-cooling, followed by stirring at room temperature for 1 hour. Water was added to the reaction mixture and extraction was effected with chloroform. The extract was dried with magnesium sulfate and the solvent was distilled off. The residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:4) and then recrystallized from ethanol to obtain 4.36 g of 8-hydroxy-5-methyl-9-(N-methyl-N-acetylamino)-7-(1-methyl-2-propenyl)-1,2,3,4,4a,9a-hexahydrofluorene.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 1 hour
  3. dry with materialThe extract was dried with magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:4)
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b4258ce49c2a41889b2d940f23855d65
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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