Triethylamine → 2-(Tetrahydro-3-furanyl)ethyl methanesulfonate

HRID 1010990Notes

Reaction equation

HRID 1010990 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][OH:8])[CH2:2]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:16][S:17]([O:8][CH2:7][CH2:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 111262252-(Oxolan-3-yl)ethan-1-ol

Product 1

HCID 576998222-(Tetrahydro-3-furanyl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Tetrahydro-3-furanyl)ethanol (230 mg) was dissolved in dry DCM (5 mL) and triethylamine (0.552 mL) was added. The stirred solution was cooled (ice bath) under nitrogen and methanesulphonyl chloride (0.199 mL) was added dropwise over 5 mins. The mixture was allowed to warm slowly to room temperature as the ice bath melted and was left for 16 h. The mixture was shaken with saturated sodium bicarbonate solution and the aqueous layer was extracted with DCM (×2). The combined organics were washed with brine, dried using a hydrophobic frit and evaporated to give the title compound (364 mg).

Workup

  1. temperatureThe stirred solution was cooled (ice bath) under nitrogen
  2. extractionthe aqueous layer was extracted with DCM (×2)
  3. washThe combined organics were washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-6d6052d02976479ead74394d279bfd66
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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