4-Toluenesulfonyl chloride → HCID 86706067, compound

HRID 2176229Notes

Reaction equation

HRID 2176229 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH:11]([OH:13])[CH3:12])[CH2:10][O:9][CH2:8][CH2:7][O:6]1)=[O:4].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1([CH:11]([O:13][S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=2)(=[O:22])=[O:21])[CH3:12])[CH2:10][O:9][CH2:8][CH2:7][O:6]1)=[O:4]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86706066HCID 86706066, compound

Product 1

HCID 86706067HCID 86706067, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(1-hydroxy-ethyl)-[1,4]dioxane-2-carboxylic acid methyl ester (1.49 g, 7.8 mmol) in pyridine (8 mL) was stirred at room temperature. 4-Toluenesulfonyl chloride (1.50 g, 7.8 mmol) was added and the reaction mixture was stirred at room temperature for 18 h. The majority of the pyridine was evaporated, 1 M hydrochloric acid was added to acidify the mixture to pH 2 and the mixture was extracted with ethyl acetate. The organic extracts were combined and washed with brine. The organic solution was filtered through a hydrophobic frit and the filtrate was evaporated. The residue was purified by silica gel chromatography using a gradient of pentane/diethyl ether 3:1 to 0:1 to afford the title compound (1.70 g, 63%) as a yellow gum and as a 3:1 mixture of diastereoisomers. LCMS (m/z) 367.0 [M+Na], Tr=2.44 min.

Workup

  1. customThe majority of the pyridine was evaporated
  2. addition1 M hydrochloric acid was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. filtrationThe organic solution was filtered through a hydrophobic frit
  6. customthe filtrate was evaporated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b2d822970b7b4958832d43f6f57a0c55
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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