Pyridine → HCID 88244643, compound

HRID 2277047Notes

Reaction equation

HRID 2277047 reaction equation
N1C=CC=CC=1.[S:7]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]1.[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16]>C(Cl)Cl.O>[CH3:22][C:21]1[CH:23]=[CH:24][C:18]([S:15]([O:14][CH2:13][CH:10]2[CH2:11][CH2:12][S:7][CH2:8][CH2:9]2)(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 201436544-(Hydroxymethyl)tetrahydro-2H-thiopyran

Product 1

HCID 88244643HCID 88244643, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Pyridine (7.6 mL, 98.4 mmol) was added at 0° C. to a solution of (tetrahydro-2H-thiopyran-4-yl)methanol (1.3 g, 9.84 mmol) in CH2Cl2 (20 mL) followed by the addition of TsCl (2.0 g, 10.83 mmol). The reaction mixture was stirred at ambient temperature for 18 h, diluted with H2O (200 mL) and extracted with CH2Cl2 (200 mL). Drying over anhydrous Na2SO4 followed by concentration in vacuo gave (tetrahydro-2H-thiopyran-4-yl)methyl 4-methylbenzenesulfonate as an off white solid. The crude was carried forward to the next step without additional purification. Yield (0.75 g, 30%).

Workup

  1. extractionextracted with CH2Cl2 (200 mL)
  2. dry with materialDrying over anhydrous Na2SO4
  3. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-48fc2193b53041fd9ad0d6be3f683515
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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