4-Toluenesulfonyl chloride → HCID 178427754, compound

HRID 874824Notes

Reaction equation

HRID 874824 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH2:12][CH2:13][CH2:14][CH:15]2[O:19][CH2:18][CH2:17][O:16]2)=[O:10])[CH2:5][CH2:4]1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1>[S:26]([O:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH2:12][CH2:13][CH2:14][CH:15]2[O:16][CH2:17][CH2:18][O:19]2)=[O:10])[CH2:5][CH2:4]1)([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 178525389HCID 178525389, compound

Product 1

HCID 178427754HCID 178427754, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice-cooled solution of trans-3-(1,3-dioxolan-2-yl)propyl 4-(hydroxymethyl)cyclohexanecarboxylate (0.306 g, 1.13 mmol) in pyridine (0.9 mL) was added para-toluenesulfonyl chloride (0.236 g, 1.24 mmol). The reaction mixture was stirred at this temperature for 1 hour and the coolant removed. The reaction mixture was stirred at RT for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with water, brine, dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was used directly without purification.

Workup

  1. customthe coolant removed
  2. stirringThe reaction mixture was stirred at RT for 18 hours
  3. additionThe reaction mixture was diluted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customthe solvent evaporated at reduced pressure
  8. customThe residue was used directly without purification

Sources & evidence

ORD record
ord-bb2f66c02a1e4b8ea407e02d6f71ef2a
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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