Pyridine → 4-Chloromethyl-4-methyl-oxazolidin-2-one

HRID 1025918ノート

反応式

HRID 1025918 の反応式
O[CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.S(Cl)([Cl:12])=O.N1C=CC=CC=1>ClCCCl>[Cl:12][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1

参加物

5

反応物 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 245546Nsc57599

生成物 1

HCID 553038834-Chloromethyl-4-methyl-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a suspension of 4-(hydroxymethyl)-4-methyloxazolidin-2-one (1.89 g, 14.4 mmol) in 1,2-dichloroethane (10 ml) was added thionyl chloride (5.0 ml, 69 mmol). The solution was stirred for 30 min at RT, and then pyridine (5.0 ml, 62 mmol) was added. The solution was heated to 90° C. for 16 h and then 110° C. for an additional 2 h, then cooled to RT and evaporated. The residue was purified by flash chromatography (30% to 100% ethyl acetate in hexanes, Rf=0.25 in 1:1 ethyl acetate:hexanes) to give the title compound as a clear oil which solidified to a white solid upon standing (1.52 g, 10.2 mmol, 71%). 1H NMR (CDCl3, 400 MHz) δ 1.49 (s, 3H), 3.55 (m, 2H), 4.12 (d, 1H, J=9.2 Hz), 4.31 (d, 1H, J=8.8 Hz), 5.4 (br s, 1H). LRMS (ESI/APCI): 150 [M+H]+.

後処理

  1. temperatureThe solution was heated to 90° C. for 16 h
  2. wait110° C. for an additional 2 h
  3. temperaturecooled to RT
  4. customevaporated
  5. customThe residue was purified by flash chromatography (30% to 100% ethyl acetate in hexanes, Rf=0.25 in 1:1 ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-df8cc368f71a48e8a29d2e1cb4473c3d
出典データセット
uspto-grants-2014_05
特許番号
US08729112B2

反応ノート

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