4-Toluenesulfonyl chloride → (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

HRID 254658

Reaction equation

HRID 254658 reaction equation
[CH2:1]([OH:7])[C@@H:2]1[O:6][CH2:5][CH2:4][CH2:3]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:7][CH2:1][C@H:2]2[CH2:3][CH2:4][CH2:5][O:6]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 6931745(2R)-oxolan-2-ylmethanol

Product 1

HCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tetrahydrofurfuryl alcohol (Lancaster, 1.0 g, 9.8 mmol) in 5 mL of CH2Cl2 and 5 mL of pyridine was added p-toluenesulfonyl chloride (2.8 g, 14.7 mmol) in portions over 15 minutes. The mixture was stirred at ambient temperature for 3 hours and was quenched with 10 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with three 5 mL portions of CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound. MS (DCI/NH3) m/z 257 (M+H)+, 274 (M+NH4)+.

Workup

  1. customwas quenched with 10 mL of saturated, aqueous NaHCO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with three 5 mL portions of CH2Cl2
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7aa0f6aec9a47e0923176cfc33732ef
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Linked notes

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