Dimethyl Sulfate → HCID 86690130、化合物

HRID 520432ノート

反応式

HRID 520432 の反応式
[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

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 86690128HCID 86690128、化合物

生成物 1

HCID 86690130HCID 86690130、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-62931d976da94964a42823c698d08987
出典データセット
uspto-grants-2016_05
特許番号
US09326973B2

反応ノート

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