3,4-dihydro-2H-pyran → Cyclohexanecarboxylic acid, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-, ethyl ester

HRID 1625032Notes

Reaction equation

HRID 1625032 reaction equation
[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[OH:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]1.[O:30]1[CH:35]=[CH:34][CH2:33][CH2:32][CH2:31]1>C(Cl)Cl>[O:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[O:18][CH:19]1[CH2:20][CH2:21][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 86973Ethyl 4-hydroxycyclohexanecarboxylateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 67249083Cyclohexanecarboxylic acid, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-, ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium-4-toluenesulfonate (2.57 g, 10.2 mmol) was added to a solution of ethyl 4-hydroxycyclohexanecarboxylate (8.8 g, 51.10 mmol) and 3,4-dihydro-2H-pyran (8.60 g, 102 mmol) in DCM (200 mL) and the reaction was stirred at rt for 16 h. The reaction was quenched with saturated aq NaHCO3. The layers were separated and the organic layer was washed with water. The organic layer was dried (Na2SO4), filtered, and concentrated. Purification via flash chromatography on a 200 g silica column using an eluent of EtOAc in hexanes (5-10%) afforded the title compound as a clear oil (11.1 g, 85%).

Workup

  1. customThe reaction was quenched with saturated aq NaHCO3
  2. customThe layers were separated
  3. washthe organic layer was washed with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via flash chromatography on a 200 g silica column

Sources & evidence

ORD record
ord-3d33a43b9eed4ceb835daac47a9eb9c5
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

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