Triethylamine → 2-(Oxan-2-yl)ethyl methanesulfonate

HRID 1010983Notes

Reaction equation

HRID 1010983 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][CH2:8][OH:9].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:17][S:18]([O:9][CH2:8][CH2:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 139481282-(Oxan-2-yl)ethan-1-ol

Product 1

HCID 576998282-(Oxan-2-yl)ethyl methanesulfonateYield 110%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Tetrahydro-2H-pyran-2-yl)ethanol (465 mg) was dissolved in dry DCM (10 mL) and triethylamine (996 mg) was added. The stirred solution was cooled in an ice bath under nitrogen and methanesulphonyl chloride (359 mg) was added dropwise over 5 mins. The reaction was allowed to warm to room temperature as the ice bath melted and was left for 16 h. The mixture was then shaken with saturated sodium bicarbonate solution and the aqueous layer was extracted with DCM (×2). The combined organic extracts were washed with brine, dried using a hydrophobic frit and evaporated to give the title compound as a brown oil (718 mg).

Workup

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

Sources & evidence

ORD record
ord-355400d2f3d942ef96adb9d895679797
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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