Triethylamine → (Tetrahydrofuran-3-yl)methyl methanesulfonate

HRID 237438Notes

Reaction equation

HRID 237438 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][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][CH2:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 139980Tetrahydro-3-furanmethanol

Product 1

HCID 22273010(Tetrahydrofuran-3-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of (tetrahydrofuran-3-yl)methanol (3.0 mL) and triethylamine (5.7 mL) in dichloromethane (30 mL) is added methanesulfonyl chloride (3.1 mL). The mixture is stirred for 12 hours at room temperature. After cooling to 0° C. triethylamine (1.3 mL) and methanesulfonyl chloride (0.7 mL) are added and the mixture is stirred for 12 hours at room temperature. The mixture is partitioned between dichloromethane and saturated aqueous NaHCO3 solution and stirred vigorously for 30 minutes. The organic phase is separated, washed with brine and dried (MgSO4). The solvent is evaporated to give the title compound. Yield: 5.6 g; TLC: rf=0.35 (silicagel, cyclohexane/ethyl acetate 1:1); Mass spectrum (ESI+): m/z=181 [M+H]+.

Workup

  1. additionare added
  2. stirringthe mixture is stirred for 12 hours at room temperature
  3. customThe mixture is partitioned between dichloromethane and saturated aqueous NaHCO3 solution
  4. stirringstirred vigorously for 30 minutes
  5. customThe organic phase is separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent is evaporated

Sources & evidence

ORD record
ord-5c61ba9ea28646fd899c358bbe6c7e33
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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