Pyridine → (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate

HRID 644035Notes

Reaction equation

HRID 644035 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[O:12]1[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]1.N1C=CC=CC=1>ClCCl>[O:12]1[CH2:17][CH2:16][CH:15]([CH2:18][O:19][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 2773573(Oxan-4-yl)methanol

Product 1

HCID 19077576(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulfonyl chloride (29.8 g, 157 mmol) was added portionwise to a mixture of tetrahydro-2H-pyran-4-yl-methanol (20.0 g, 172 mmol) and pyridine (25.2 mL, 313 mmol) in dichloromethane (200 ml). The mixture was stirred at room temperature for 17 h, then quenched with aqueous hydrochloric acid (2 M; 100 ml). The layers were separated and the aqueous layer extracted with dichloromethane (2×100 ml). The organic layers were combined and concentrated in vacuo. Recrystallisation from dichloromethane: heptane (5:1) afforded toluene-4-sulfonic acid tetrahydro-pyran-4yl-methyl ester. The mother liquors were further purified by silica gel column chromatography eluting with 50% dichloromethane in n-heptane to yield a further quantity of toluene-4-sulfonic acid tetrahydro-pyran-4yl-methyl ester (total yield 41.6 g, 154 mmol).

Workup

  1. customquenched with aqueous hydrochloric acid (2 M; 100 ml)
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with dichloromethane (2×100 ml)
  4. concentrationconcentrated in vacuo
  5. customRecrystallisation from dichloromethane: heptane (5:1)

Sources & evidence

ORD record
ord-85591238916a4a038ad6ce486e4b9c1d
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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