Triethylamine → Oxolane-3,4-diyl dimethanesulfonate

HRID 541478Notes

Reaction equation

HRID 541478 reaction equation
[O:1]1[CH2:5][CH:4]([OH:6])[CH:3]([OH:7])[CH2:2]1.C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[CH3:15][S:16]([O:7][CH:3]1[CH:4]([O:6][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:5][O:1][CH2:2]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 908031,4-Anhydrothreitol

Product 1

HCID 325978Oxolane-3,4-diyl dimethanesulfonateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
2.5 °C

Procedure

Into a round-bottom flask, was placed a solution of tetrahydrofuran-3,4-diol (500 mg, 4.80 mmol, 1.00 equiv) and triethylamine (1.45 g, 14.3 mmol, 3.00 equiv) in dichloromethane (8 mL). The mixture was cooled to 0-5° C. and a solution of methanesulfonyl chloride (1.40 g, 12.2 mmol, 2.50 equiv) in dichloromethane (2 mL) was added drop-wise. The solution was stirred at room temperature for 2 h, and then diluted with dichloromethane (100 mL). The solution was washed with aqueous NH4Cl (2×30 mL) then brine (30 mL), dried (Na2SO4), filtered and concentrated in vacuum to obtain the title compound as a brown solid (1.00 g, 72%).

Workup

  1. customInto a round-bottom flask, was placed
  2. washThe solution was washed with aqueous NH4Cl (2×30 mL)
  3. dry with materialbrine (30 mL), dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-85b0950087b74128aba705541f11056d
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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