Methanesulfonyl chloride → Methyl 3-[2-[(methylsulfonyl)oxy]ethyl]-1-naphthalenecarboxylate

HRID 337603Notes

Reaction equation

HRID 337603 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.CCN(C(C)C)C(C)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:27][S:28]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66896170Methyl 3-(2-hydroxyethyl)-1-naphthalenecarboxylate

Product 1

HCID 86651673Methyl 3-[2-[(methylsulfonyl)oxy]ethyl]-1-naphthalenecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a dichloromethane (0.03 M) solution of methyl 3-(2-hydroxyethyl)-1-naphthalenecarboxylate (1 eq.) from Step 2, Amine 31 and Hunig's base (1.5 eq.) was added at 0 methanesulfonyl chloride (1.3 eq.). The resulting solution was stirred at 0° C. for 30 min and then at RT for 15 min. The reaction mixture was subsequently quenched with 10% aq. HCl. The aqueous wash was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, and filtered. Concentration of the filtrate in vacuo afforded the crude title compound as a colorless oil.

Workup

  1. waitat RT for 15 min
  2. customThe reaction mixture was subsequently quenched with 10% aq. HCl
  3. washThe aqueous wash
  4. customwas separated
  5. extractionback-extracted with ether
  6. washThe combined organic extracts were washed further with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-000c422fc2324db0bf00c579bcb36652
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…