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

HRID 536720Notes

Reaction equation

HRID 536720 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][OH:7].[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:7][CH2:6][C@H:2]2[CH2:3][CH2:4][CH2:5][O:1]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

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

Product 1

HCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonateYield 69.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-(tetrahydrofuran-2-yl)methanol (1.0 g, 9.8 mmol) in CH2Cl2 (3 mL) and pyridine (3 mL) at ambient temperature was added 4-methylbenzene-1-sulfonyl chloride (2.0 g, 10.3 mmol) portionwise over 5 min. The mixture was stirred for 16 hours at ambient temperature then quenched by the addition of 5% aqueous HCl (10 mL). The layers were separated and the aqueous phase was extracted with CH2Cl2 (3×5 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 75% hexanes in EtOAc) to afford the title compound (1.7 g, 6.8 mmol, 69% yield). MS (DCI/NH3) m/z 257 (M+H)+ and 274 (M+NH4)+.

Workup

  1. customthen quenched by the addition of 5% aqueous HCl (10 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (3×5 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (SiO2, 75% hexanes in EtOAc)

Sources & evidence

ORD record
ord-0f0e42990490420aa8c8bdf8ca3dec27
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

Loading…