ethyl 4-hydroxycyclohexane-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of ethyl 4-hydroxycyclohexanecarboxylate (16 g, 93 mmol), 4-methylmorpholine N-oxide (16.32 g, 139.5 mmol) and CH2Cl2 (180 mL) was added tetrapropylammonium perruthenate (0.8 g, 2.3 mmol) in small portions at a rate that maintained the reaction temperature at 35-40°. The reaction slowly cooled and was stirred overnight. The resulting mixture was filtered through silica with CH2Cl2 to afford 13.46 g (85%) of the title compound as a colorless oil. 1H NMR (CDCl3): d 4.19 (q, 2), 2.75 (m, 1), 2.5 (m, 2), 2.37 (m, 2), 2.19 (m, 2), 2.04 (m, 2). maintained the reaction temperature at 35-40° The reaction slowly cooled The resulting mixture was filtered through silica with CH2Cl2