Pyridine → HCID 10878028, compound

HRID 12489Notes

Reaction equation

HRID 12489 reaction equation
[OH:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4](=[O:6])[CH3:5].N1C=CC=CC=1.[S:15](Cl)([CH3:18])(=[O:17])=[O:16]>C(Cl)Cl>[CH3:7][C:3]([CH3:8])([C:4](=[O:6])[CH3:5])[CH2:2][O:1][S:15]([CH3:18])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 111943184-Hydroxy-3,3-dimethylbutan-2-one

Product 1

HCID 10878028HCID 10878028, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

23.7 g 4-Hydroxy-3,3-dimethyl-butan-2-one was dissolved in 150 mL DCM. 49.5 mL (3 eq) pyridine and 17.5 mL (1.1 eq) mesylchloride were added and the mixture was stirred at room temperature for 20 hours. The suspension was filtered and the filter cake was washed two times with DCM. The filtrate was washed with 1 M HCl and the aqueous layer was extracted two times with DCM. The combined filtrates were dried over Na2SO4 and the solvent was evaporated under reduced pressure to give 41.2 g of a brown liquid. 1H NMR (400 MHz, CDCl3) δ 1.24 (s, 6H), 2.20 (s, 3H), 3.03 (s, 3H), 4.21 (s, 2H).

Workup

  1. filtrationThe suspension was filtered
  2. washthe filter cake was washed two times with DCM
  3. washThe filtrate was washed with 1 M HCl
  4. extractionthe aqueous layer was extracted two times with DCM
  5. dry with materialThe combined filtrates were dried over Na2SO4
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-47839d9892c84994b6ebb315809c5146
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Reaction notes

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