Pyridine → (4-methoxytetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate

HRID 1623247Notes

Reaction equation

HRID 1623247 reaction equation
[CH3:1][O:2][C:3]1([CH2:9][OH:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[C:11]1(C)[C:12]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=1.N1C=CC=C[CH:23]=1>>[CH3:23][C:15]1[CH:16]=[CH:11][C:12]([S:17]([O:10][CH2:9][C:3]2([O:2][CH3:1])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)(=[O:18])=[O:19])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 66937097(4-methoxyoxan-4-yl)methanol

Product 1

HCID 58127128(4-methoxytetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate

Conditions

Temperature
25 °C

Procedure

To a solution of (4-methoxytetrahydro-2H-pyran-4-yl)methanol (300 mg, 2.05 mmol) in pyridine (4 ml) at ambient temperature was added toluenesulfonic chloride (430 mg, 2.25 mmol) and the resulting mixture was stirred overnight at about 25° C. The stirred mixture was concentrated and the solid residue was dissolved in DCM and purified by silica gel chromatography using a 12 g column, eluting with 0-30% ethyl acetate in heptane to yield the desired compound “O” as a light yellow solid (360 mg). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.45-1.63 (m, 2H) 1.61-1.79 (m, 2H) 2.46 (s, 3H), 3.16 (s, 3H) 3.53-3.75 (m, 4H) 3.93 (s, 2H), 7.36 (d, J=8.20 Hz, 2H) 7.81 (d, J=8.20 Hz, 2H).

Workup

  1. concentrationThe stirred mixture was concentrated
  2. dissolutionthe solid residue was dissolved in DCM
  3. custompurified by silica gel chromatography
  4. washeluting with 0-30% ethyl acetate in heptane

Sources & evidence

ORD record
ord-dca7d2b08e84453b85741688eb2ca4ab
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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