Triethylamine → Oxan-4-ylmethyl methanesulfonate

HRID 1487028Notes

Reaction equation

HRID 1487028 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([O:8][CH2:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2773573(Oxan-4-yl)methanol

Product 1

HCID 15166436Oxan-4-ylmethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(Tetrahydro-2H-pyran-4-yl)methanol (29.9 mg, 0.257 mmol) was dissolved in dichloromethane (DCM) (4 mL). To this solution was added triethylamine (0.108 mL, 0.772 mmol). The reaction was cooled to 0° C., methanesulfonyl chloride (0.03 mL, 0.386 mmol) added and the reaction left to stir overnight, allowing the reaction to warm to 20° C. The reaction was concentrated in vacuo. The product was partitioned between ethyl acetate (20 mL) and aqueous saturated sodium bicarbonate (20 mL). The organic phase was dried and concentrated in vacuo, before being used in the next reaction with no further purification or characterisation, 49 mg.

Workup

  1. waitthe reaction left
  2. customthe reaction
  3. temperatureto warm to 20° C
  4. concentrationThe reaction was concentrated in vacuo
  5. customThe product was partitioned between ethyl acetate (20 mL) and aqueous saturated sodium bicarbonate (20 mL)
  6. customThe organic phase was dried
  7. concentrationconcentrated in vacuo
  8. custombefore being used in the next reaction with no further purification or characterisation, 49 mg

Sources & evidence

ORD record
ord-abe18a0d15ec463eb0474ba755a4d2b6
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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