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

HRID 1183936Notes

Reaction equation

HRID 1183936 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 ester

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). After 16 hours the reaction was quenched with saturated aqueous sodium bicarbonate. The layers were separated and the organic layer was washed with water. The organic layer was dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography on an Analogix SF65-200 g column (hexanes/ethyl acetate 95:05-9:1) afforded the title compound (clear oil) as a mixture of isomers (11.1 g, 85%).

Workup

  1. customAfter 16 hours the reaction was quenched with saturated aqueous sodium bicarbonate
  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 by flash column chromatography on an Analogix SF65-200 g column (hexanes/ethyl acetate 95:05-9:1)

Sources & evidence

ORD record
ord-baec3c736fa84908bbc936dd97e00f95
Source dataset
uspto-grants-2014_03
Patent number
US08664401B2

Reaction notes

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