Dimethyl Sulfate → HCID 86690130, compound

HRID 520432Notes

Reaction equation

HRID 520432 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1.S(OC)(O[CH3:20])(=O)=O>C1COCC1>[CH3:20][O:3][CH2:4][C:5]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 86690128HCID 86690128, compound

Product 1

HCID 86690130HCID 86690130, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% NaH (40.3 mg, 1.007 mmol) was added to a cold (−20° C.) solution of ethyl 2-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate (158 mg, 0.839 mmol) in THF (3 mL) and the mixture was allowed to warm to rt over ˜30 min. Neat dimethyl sulfate (127 mg, 1.007 mmol) was added at 0° C. and allowed to warm to rt and stirred overnight. Excess dimethyl sulfate was quenched with TEA, and then acidified with 1N HCl, product was extracted with ether, washed with water, brine and dried (MgSO4). Crude isolate was purified by silica gel FCC (0-2% MeOH in DCM) to afford ethyl 2-(methoxymethyl)tetrahydro-2H-pyran-2-carboxylate. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.34-4.22 (m, J=7.2, 7.2, 7.2, 4.1 Hz, 2H), 3.96-3.87 (m, 1H), 3.86-3.77 (m, 1H), 3.55-3.43 (m, 2H), 3.36 (s, 3H), 2.17-2.07 (m, 1H), 1.80-1.70 (m, 1H), 1.69-1.56 (m, 2H), 1.55-1.42 (m, 3H), 1.32 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureto warm to rt
  2. customExcess dimethyl sulfate was quenched with TEA
  3. extractionwas extracted with ether
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customCrude isolate
  7. customwas purified by silica gel FCC (0-2% MeOH in DCM)

Sources & evidence

ORD record
ord-62931d976da94964a42823c698d08987
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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