Hydrochloric Acid → HCID 70906909, compound

HRID 2200379Notes

Reaction equation

HRID 2200379 reaction equation
CC1(C)CO[C:5]2([CH2:9][C@@H:8]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:7][CH2:6]2)[O:4]C1.Cl>C(O)C>[O:4]=[C:5]1[CH2:6][CH2:7][C@H:8]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131735706HCID 131735706, compound

Product 1

HCID 70906909HCID 70906909, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (S)-benzyl 8,8-dimethyl-6,10-dioxaspiro[4.5]decane-2-carboxylate (3.5 g, 11.50 mmol) in ethanol (50 ml) at 0° C. was added 0.1 N hydrochloric acid (17.5 ml) drop wise. The reaction was stirred at 25° C. for overnight. Upon completion, the reaction mixture was concentrated under reduced pressure; the residue was dissolved in dichloromethane (50 ml) and diluted with water (25 ml). The organic mass was extracted using dichloromethane (2×50 ml) and the combined organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography over silica gel using ethyl acetate in hexane as eluents to obtain (S)-benzyl 3-oxocyclopentanecarboxylate (2 g, 80%).

Workup

  1. concentrationUpon completion, the reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (50 ml)
  3. additiondiluted with water (25 ml)
  4. extractionThe organic mass was extracted
  5. dry with materialthe combined organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-d22fb6611f124a5db9027e18b282dc62
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

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