Oxalyl chloride → TETRAHYDROPYRAN-2-CARBONYL CHLORIDE

HRID 553609Notes

Reaction equation

HRID 553609 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([OH:9])=O.C(Cl)(=O)C([Cl:13])=O>C(Cl)Cl.CN(C=O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([Cl:13])=[O:9]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 10964532Oxane-2-carboxylic acid

Product 1

HCID 15731743TETRAHYDROPYRAN-2-CARBONYL CHLORIDEYield 99.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tetrahydro-pyran-2-carboxylic acid (6.94 g, 47.96 mmol) in DCM (200 mL) are added oxalyl chloride (4.81 mL, 56.83 mmol) as a solution in DCM (50 mL) and DMF (3 drops). The reaction is stirred at room temperature for 18 h, then concentrated under reduced pressure to afford 7.1 g of tetrahydro-pyran-2-carbonyl chloride, which is used in the next step. Yield: 99%; by 58° C., 1 mm Hg; 1H NMR (250 MHz, CHLOROFORM-d) δ ppm 1.49-1.98 (5H, m), 2.02-2.19 (1H, m), 3.46-3.66 (1H, m), 3.96-4.12 (1H, m), 4.24 (1H, dd, J=9.14, 3.20 Hz)

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72e228673cd54a3d82402d2dadfb15aa
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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