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

HRID 2277037Notes

Reaction equation

HRID 2277037 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[O:12]1[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]1.CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[CH3:8][C:7]1[CH:9]=[CH:10][C:4]([S:1]([O:19][CH2:18][CH:15]2[CH2:16][CH2:17][O:12][CH2:13][CH2:14]2)(=[O:3])=[O:2])=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 2773573(Oxan-4-yl)methanol

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

TsCl (7.22 g, 37.9 mmol) was added portionwise to a solution of alcohol (9) (4.0 g, 34.44 mmol), Et3N (7.0 g, 69 mmol) and DMAP (0.05 g, 0.35 mmol) in dry DCM (50 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and further stirred for 1 h. The reaction mixture was diluted with water, extracted with EtOAc, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give (tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzene-sulfonate (10) as white solid. Yield (8.5 g, 91%); 1H NMR (400 MHz, DMSO-d6) δ 7.78 (d, J=8.0 Hz, 2H), 7.48 (d, J=8.0 Hz, 2H), 3.87 (d, J=6.4 Hz, 2H), 3.78 (dd, J=11.2, 4.2 Hz, 2H), 3.22 (dt, J=11.6, 1.6 Hz, 2H), 2.42 (s, 3H), 1.88-1.79 (m, 1H), 1.46 (dd, J=12.8, 1.6 Hz, 2H), 1.18-1.07 (m, 2H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b5530c229d94534a78ea4cc0d1b0930
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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