Calcium Carbonate → 6-[3-[4-(1-Pyrrolidinyl)phenyl]propoxy]-2-hexanone

HRID 1721965Notes

Reaction equation

HRID 1721965 reaction equation
[CH3:1][C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)SCCCS1.C(=O)([O-])[O-:28].[Ca+2]>C1COCC1.CO.O.[Hg](Cl)Cl>[N:22]1([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][CH2:9][CH2:8][C:2](=[O:28])[CH3:1])=[CH:17][CH:18]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 2

HCID 10112Calcium CarbonateHCID 198627331-[4-[3-[4-(2-Methyl-1,3-dithian-2-yl)butoxy]propyl]phenyl]pyrrolidine

Product 1

HCID 198627016-[3-[4-(1-Pyrrolidinyl)phenyl]propoxy]-2-hexanone

Reagents, catalysts & solvents 3

HCID 24085Mercuric ChlorideCatalystHCID 8028TetrahydrofuranSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of the product of stage (iv) (3.2 g) in THF (50 ml) was added to a stirred suspension of mercury (II) chloride (8.5 g) and calcium carbonate (3.2 g) in methanol-water (9:1, 50 ml) and the mixture was stirred at reflux for 1 h. The reaction was filtered through hyflo, the filtrate was concentrated in vacuo and the resulting oil was dissolved in chloroform (50 ml). The resulting precipitate was removed by filtration, the solvent was evaporated and the residue was purified by FCC (System D 19:1→4:1) to give the title compound as a crystalline mass (1.4 g) m.p. 30°-31°.

Workup

  1. temperatureat reflux for 1 h
  2. filtrationThe reaction was filtered through hyflo
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionthe resulting oil was dissolved in chloroform (50 ml)
  5. customThe resulting precipitate was removed by filtration
  6. customthe solvent was evaporated
  7. customthe residue was purified by FCC (System D 19:1→4:1)

Sources & evidence

ORD record
ord-5f2ef6d99d184d2296edef7dfc469a1a
Source dataset
uspto-grants-1989_08
Patent number
US04853381

Reaction notes

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