Triethylamine → (Tetrahydrofuran-3-yl)methyl methanesulfonate

HRID 1010980Notes

Reaction equation

HRID 1010980 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]>C(Cl)Cl>[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 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 139980Tetrahydro-3-furanmethanol

Product 1

HCID 22273010(Tetrahydrofuran-3-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To tetrahydro-3-furanmethanol (25 g) in dry DCM (250 mL) at 0° C. under nitrogen was added triethylamine (68 mL) in a single portion. Methanesulphonyl chloride (24.7 mL) was added dropwise over 15 mins. The reaction was warmed to room temperature and was left over a weekend. The mixture was taken up in DCM (50 mL) and washed with saturated sodium bicarbonate solution (100 mL). The organics were dried using a hydrophobic frit and concentrated in vacuo to give the title compound as a brown oil in quantitative yield.

Workup

  1. waitwas left over a weekend
  2. washwashed with saturated sodium bicarbonate solution (100 mL)
  3. customThe organics were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86ee9fb3d02f4ebc998ba4b85edd515e
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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