Triethylamine → (2,2-Dimethyltetrahydro-2H-pyran-4-yl)methyl methanesulfonate

HRID 1010986Notes

Reaction equation

HRID 1010986 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH:6]([CH2:8][OH:9])[CH2:5][CH2:4][O:3]1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:18][S:19]([O:9][CH2:8][CH:6]1[CH2:5][CH2:4][O:3][C:2]([CH3:10])([CH3:1])[CH2:7]1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 51072184(2,2-Dimethyloxan-4-yl)methanol

Product 1

HCID 57699693(2,2-Dimethyltetrahydro-2H-pyran-4-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2,2-Dimethyltetrahydro-2H-pyran-4-yl)methanol (2.54 g) was dissolved in dry DCM (40 mL) and triethylamine (4.9 mL) was added with stirring. The solution was cooled (ice bath) under nitrogen and methanesulphonyl chloride (1.77 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 (3.93 g).

Workup

  1. temperatureThe 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-51fe6cbff75b48ea9fc143880c057895
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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