Triethylamine → (R)-methyl 4-(1-(methylsulfonyloxy)butyl)benzoate

HRID 537524Notes

Reaction equation

HRID 537524 reaction equation
[OH:1][C@@H:2]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(OC)(C)(C)C>[CH3:23][S:24]([O:1][C@@H:2]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68157820(R)-methyl 4-(1-hydroxybutyl)benzoate

Product 1

HCID 86669087(R)-methyl 4-(1-(methylsulfonyloxy)butyl)benzoate

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of (R)-methyl 4-(1-hydroxybutyl)benzoate, intermediate (26) (10 g, 48 mmol) in methyl t-butyl ether (80 mL) containing triethylamine (6.32 g, 62 mmol) was added methanesulfonyl chloride (6.05 g, 53 mmol) slowly at 20° C. The solution was filtered to remove triethylamine salts and the solution used in the next step without isolation.

Workup

  1. filtrationThe solution was filtered
  2. customto remove triethylamine salts

Sources & evidence

ORD record
ord-3b01d3b2fafe469caf250fc88749dd85
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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