Triethylamine → Oxan-4-yl methanesulfonate

HRID 1052250Notes

Reaction equation

HRID 1052250 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][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][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 74956Tetrahydro-4H-pyran-4-ol

Product 1

HCID 11344352Oxan-4-yl methanesulfonateYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tetrahydro-4H-pyran-4-ol (100.0 μL, 1.05 mmol) in methylene chloride (8.0 mL) at 0° C., triethylamine (183 μL, 1.31 mmol) and methanesulfonyl chloride (89.3 μL, 1.15 mmol) were added sequentially. After 1.5 h, the reaction was quenched with water and extracted with methylene chloride. The combined organic layers were dried over MgSO4, and then concentrated to give the desired product (190 mg, 100%), which was used directly in the next step. 1H NMR (400 MHz, CDCl3): δ 4.92-4.87 (m, 1H), 3.97-3.92 (m, 2H), 3.57-3.52 (m, 2H), 3.04 (s, 3H), 2.07-2.02 (m, 2H), 1.92-1.83 (m, 2H) ppm.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ebbab1bd483d45c9ad23189748dbc433
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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