Hydrochloric Acid → HCID 13880243, compound

HRID 917898Notes

Reaction equation

HRID 917898 reaction equation
COC1C=C2[C@@:13]34[C@@H:17]5[CH2:18][C@H:19]6C(CN5[CH2:15][CH2:14]3)=CC[O:25][C@H:21]3[CH2:22][C:23](=[O:24])N([C@H]4[C@@H:20]63)C2=CC=1OC.C[C@@]12[C@H]3CC[C@]4(C)[C@@H](C(CO)=O)CC[C@H]4[C@@H]3CC[C@@H]1CC(=[O:35])CC2.Cl.[C:55]([O:58][CH2:59]C)(=[O:57])[CH3:56]>>[C:55]([CH2:56][CH2:15][CH2:14][CH2:13][CH2:17][CH2:18][CH:19]1[C:20](=[O:35])[C@H:21]([OH:25])[CH2:22][C:23]1=[O:24])([O:58][CH3:59])=[O:57]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 131710384HCID 131710384, compound

Product 1

HCID 13880243HCID 13880243, compound

Procedure

The resolved brucine-hydroxydione salt (2.2 g) was dissolved in ethyl acetate (30 ml). To this solution 30 ml of 0.25 N HCl was added and the heterogeneous mixture was stirred very vigorously for 2 minutes. Upon standing two layers formed and were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers from the two extractions were combined and were washed with water and saturated brine solution and were dried over anhydrous magnesium sulfate. Evaporation of the solvent gave 2-(6'-carbomethoxyhexyl)-4(R)-hydroxy-cyclopentane-1,3-dione as a white crystalline solid (780 mg).

Workup

  1. customformed
  2. customwere separated
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. extractionThe organic layers from the two extractions
  5. washwere washed with water and saturated brine solution
  6. dry with materialwere dried over anhydrous magnesium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-88bba62910aa479c844b9058d728ae5f
Source dataset
uspto-grants-1976_07
Patent number
US03968141

Reaction notes

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