4-Toluenesulfonyl chloride → HCID 12641003, compound

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][O:8][S:15]([C:12]1[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=1)(=[O:17])=[O:16]

Participants

Reactant 4

HCID 73974-Toluenesulfonyl chloride

HCID 7524Tetrahydropyran-2-methanol

HCID 8471Triethylamine

HCID 516892Sodium Bicarbonate

Product 1

HCID 12641003HCID 12641003, compound

Conditions

Temperature: 0 °C

Procedure

To a suspension of tetrahydropyran-2-methanol (2 g, 17.2 mmol) cooled at 0° C. is added toluene-4-sulfonyl chloride (3.6 g, 18.92 mmol), followed by (2.63 mL , 18.92 mmol) of triethylamine. The mixture is allowed to reach RT and stirred overnight. Then poured into an aqueous saturated solution of NaHCO3. The layers are separated and the aqueous one extracted twice with CH2Cl2. The combined organic extracts are dried over Na2SO4, filtered and concentrated. The crude material is purified by flash chromatography on silica gel (eluent: c-hexane/AcOEt 80:20) to give the title product. TLC, Rf (CH2Cl2/MeOH 95:5)=0.9. MS (LC-MS): 271.1 [M+H]+, tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, flow: 1.5 ml/min): 5.32 min.