4-Toluenesulfonyl chloride → HCID 12641003, compound

HRID 1158427Notes

Reaction equation

HRID 1158427 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

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 7524Tetrahydropyran-2-methanolHCID 8471TriethylamineHCID 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.

Workup

  1. customto reach RT
  2. customThe layers are separated
  3. extractionthe aqueous one extracted twice with CH2Cl2
  4. dry with materialThe combined organic extracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material is purified by flash chromatography on silica gel (eluent: c-hexane/AcOEt 80:20)

Sources & evidence

ORD record
ord-f7613a7e9e1d4be1bb24bd8285d934af
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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