Dimethyl Sulfate → HCID 86690130, 화합물

HRID 520432노트

반응식

HRID 520432 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 86690130HCID 86690130, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-62931d976da94964a42823c698d08987
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326973B2

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