Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 11019155, compound

HRID 628818Notes

Reaction equation

HRID 628818 reaction equation
[OH:1][C@H:2]([CH2:8][C:9]1([CH3:14])OCC[O:10]1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>CC(C)=O.O>[OH:1][C@H:2]([CH2:8][C:9](=[O:10])[CH3:14])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 90356733HCID 90356733, compound

Product 1

HCID 11019155HCID 11019155, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of Methyl(3R)-3-hydroxy-4-(2-methyl-1,3-dioxolan-2-yl)butanoate (3) (5 g, 24.5 mmol) (as prepared in Experiment 15) in a mixture of acetone/water (2:1, 30 mL), pyridiniumtosylate (1.84 g, 7.34 mmol) was added and the reaction mixture was refluxed (60° C.) for 1-2 hours. After removing the solvent under vacuum, a 10% NaHCO3 solution was added and extracted with dichloromethane (3×30 mL). The combined organic phases was evaporated under reduced pressure to give methyl(3R)-3-hydroxy-5-oxohexanoate (6) as an oil (3.33 g, 85%).

Workup

  1. additionwas added
  2. customAfter removing the solvent under vacuum
  3. additiona 10% NaHCO3 solution was added
  4. extractionextracted with dichloromethane (3×30 mL)
  5. customThe combined organic phases was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f2fb795c09d94e2a85fbdbd243d67cf1
Source dataset
uspto-grants-2016_04
Patent number
US09315470B2

Reaction notes

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