Ethyl Acetate → 1-(4-Hydroxycyclohexyl)propan-1-one

HRID 626109Notes

Reaction equation

HRID 626109 reaction equation
[CH3:1][CH2:2][Mg+].[Br-].[OH:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12](N(OC)C)=[O:13])[CH2:8][CH2:7]1.CCOC(C)=O>C1COCC1>[OH:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:13])[CH2:2][CH3:1])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 86642922HCID 86642922, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 510398611-(4-Hydroxycyclohexyl)propan-1-oneYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

EtMgBr (1 M, 3.0 eq, 20 mL) was added to a solution of 4-hydroxy-N-methoxy-N-methylcyclohexanecarboxamide (1.0 g, 1.0 eq) in dry THF at 0° C. Once addition was complete, the mixture was stirred overnight. The reaction mixture was washed with saturated NH4Cl (aq), and extracted by EtOAc. The extract was dried, concentrated, and purified by column chromatography with petroleum ether:EtOAc=1:1 to give the desired product (0.6 g, 72% yield). 1H NMR (400 MHz, CDCl3) δ 3.50-3.64 (m, 1H), 2.47 (q, J=7.2 Hz, 2H), 2.28-2.37 (m, 1H), 2.00-2.10 (m, 2H), 1.88-1.94 (m, 2H), 1.70-1.80 (m, 1H), 1.21-1.49 (m, 4H), 1.05 (t, J=7.2 Hz, 3H).

Workup

  1. additionOnce addition
  2. washThe reaction mixture was washed with saturated NH4Cl (aq)
  3. extractionextracted by EtOAc
  4. customThe extract was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography with petroleum ether

Sources & evidence

ORD record
ord-9f37ee00452a44258c65951390588349
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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