p-Toluenesulfonic acid → 1-ethyl 1-(tetrahydro-2H-pyran-2-yloxy)cyclopropanecarboxylate

HRID 1503300

Reaction equation

HRID 1503300 reaction equation
[OH:1][C:2]1([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:4][CH2:3]1.CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:21]1[CH2:26][O:25][CH:24]=[CH:23][CH2:22]1>C(Cl)Cl>[O:25]1[CH2:26][CH2:21][CH2:22][CH2:23][CH:24]1[O:1][C:2]1([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 2733706Ethyl 1-hydroxycyclopropane-1-carboxylate

Product 1

HCID 900103401-ethyl 1-(tetrahydro-2H-pyran-2-yloxy)cyclopropanecarboxylateYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 1-hydroxycyclopropanecarboxylate (1040 mg, 8.000 mmol) and PTSA (137 mg, 0.800 mmol) in DCM (20 mL) was added a solution of DHP (1344 mg, 16.00 mmol) in DCM (10 mL) dropwise at 0° C. The mixture was stirred for 20 h at room temperature. After concentration, the residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (10/1) to afford the title compound (1500 mg, 85%) as oil. LC-MS (ESI): m/z=215 (M+H)+.

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with petroleum ether/ethyl acetate (10/1)

Sources & evidence

ORD record
ord-63720363da2249dfab3a43238ad45427
Source dataset
uspto-grants-2015_12
Patent number
US09212173B2

Linked notes

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