Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate → Ethyl 1-methyl-4-oxocyclohexanecarboxylate

HRID 1948087

Reaction equation

HRID 1948087 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH3:16])[CH2:15][CH2:14][C:9]2(OCC[O:10]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C1COCC1.Cl.CCOC(C)=O>[CH3:16][C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8][C:9](=[O:10])[CH2:14][CH2:15]1

Participants

5

Reactant 1

HCID 19004805Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate2×

Product 1

HCID 21911973Ethyl 1-methyl-4-oxocyclohexanecarboxylate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-Methyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (Compound 282G) was dissolved in THF (20 mL) and 3N aq. HCl (30 mL). The resulting mixture was stirred at rt overnight. The mixture was diluted with EtOAc (50 mL), washed with brine (20 mL), and dried over anhydrous sodium sulfate. 1H NMR (CDCl3): 1.28 (t, J=7.1 Hz, 3H), 1.29 (s, 3H), 1.63-1.70 (m, 2H), 2.30-2.74 (m, 6H), 3.94 (s, 4H), 4.19 (q, J=7.1 Hz, 2H).

Workup

  1. washwashed with brine (20 mL)
  2. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-cf2f42129ff544f59ad46f0b76416fc3
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Linked notes

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