4-Toluenesulfonyl chloride → (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate

HRID 1470040Notes

Reaction equation

HRID 1470040 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[S:9](Cl)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10]>C(N(CC)CC)C>[CH3:16][C:15]1[CH:17]=[CH:18][C:12]([S:9]([O:8][CH2:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 2773573(Oxan-4-yl)methanol

Product 1

HCID 19077576(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Commercially available (tetrahydro-2H-pyran-4-yl)methanol (Maybridge), tosyl chloride and triethylamine were processed using the method described in Example 184B to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.05-1.25 (m, 2H), 1.40-1.53 (m, 2H), 1.73-1.94 (m, 1H), 2.43 (s, 3H), 3.14-3.28 (m, 2H), 3.71-3.84 (m, 2H), 3.88 (d, J=6.4 Hz, 2H), 7.48 (d, J=8.5 Hz, 2H), 7.79 (d, J=8.5 Hz, 2H).

Sources & evidence

ORD record
ord-3fda7e486de548d9b4b9cd9b06eaed70
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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