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

HRID 511518

Reaction equation

HRID 511518 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-032125fac29c4d34aa975832e3801ba5
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Linked notes

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