Triethylamine → Methanesulfonic acid 2-[3-(2-methanesulfonyloxy-ethyl)-oxetan-3-YL]-ethyl ester

HRID 1850310Notes

Reaction equation

HRID 1850310 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([CH2:8][CH2:9][OH:10])[CH2:7][O:6][CH2:5]1.CCN(CC)CC.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl.O>[CH3:18][S:19]([O:1][CH2:2][CH2:3][C:4]1([CH2:8][CH2:9][O:10][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:7][O:6][CH2:5]1)(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 585475403,3-Oxetanediethanol

Product 1

HCID 86660168Methanesulfonic acid 2-[3-(2-methanesulfonyloxy-ethyl)-oxetan-3-YL]-ethyl esterYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[3-(2-Hydroxy-ethyl)-oxetan-3-yl]-ethanol (123) (1.3 g, 8.9 mmol) in CH2Cl2 (20 mL) at 0° C. was added Et3N (2.7 g, 26.7 mmol) and methanesulfonyl chloride (2.0 g, 17.8 mmol). The solution was allowed to warm to RT and stirred for 15 min. The reaction mixture was diluted with water (80 mL). The aqueous phase was extracted with CH2Cl2 (3×50 mL) and the combined organic extracts were washed with brine (100 mL), dried over MgSO4, filtered, and concentrated to give the product (124) (2.0 g, 6.6 mmol, yield: 74%). ESI-MS (M+1): 303 calc. for C9H18O7S2 302.

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2 (3×50 mL)
  2. washthe combined organic extracts were washed with brine (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dac41a9bd69349a7824f0259369033a3
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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