4-Toluenesulfonyl chloride → HCID 51900550, compound

HRID 553611Notes

Reaction equation

HRID 553611 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H: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>N1C=CC=CC=1>[CH3:19][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:8][CH2:7][C@@H:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 6950811(2S)-oxan-2-ylmethanol

Product 1

HCID 51900550HCID 51900550, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.18 g (18.75 mmol) of (2S)-oxan-2-ylmethanol in pyridine (25 mL) are added 7.15 g (37.5 mmol) of p-toluenesulfonylchloride portionwise at 10° C. After complete addition the reaction is allowed to warm to room temperature and stirred for 18 h. The reaction is poured onto a stirred mixture of 6M aqueous HCl/ice. The mixture is extracted with DCM (3×25 mL). The organic layer is dried (MgSO4), filtered and the filtrate is concentrated under reduced pressure to give 3.91 g of (2S)-oxan-2-ylmethyl 4-methylbenzene-1-sulfonate. Yield: 76%, ES-MS: m/z: 293 [M+Na]; 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.21-1.32 (1H, m), 1.41-1.60 (4H, m), 1.80-1.90 (1H, m), 2.45 (3H, s), 3.37 (1H, td, J=11.41, 2.82 Hz), 3.48-3.58 (1H, m), 3.89-3.98 (3H, m), 7.34 (2H, d, J=8.09 Hz), 7.80 (2H, d, J=8.24 Hz).

Workup

  1. additionAfter complete addition the reaction
  2. extractionThe mixture is extracted with DCM (3×25 mL)
  3. dry with materialThe organic layer is dried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-2901abe11a184c5182f0af85c7bf9b6f
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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