Methyl chloroformate → HCID 59642988、化合物

HRID 2251613ノート

反応式

HRID 2251613 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)([CH3:3])[CH3:2].[Li]CCCC.Cl[C:22]([O:24][CH3:25])=[O:23].CCOC(C)=O>C1COCC1.CCCCCC>[CH:1]([C:4]1[CH:5]=[C:6]([O:14][CH3:15])[C:7]([O:10][CH2:11][O:12][CH3:13])=[C:8]([CH:9]=1)[C:22]([O:24][CH3:25])=[O:23])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 6586Methyl chloroformateHCID 8857Ethyl AcetateHCID 59643052HCID 59643052、化合物HCID 178418339Butyllithium

生成物 1

HCID 59642988HCID 59642988、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-isopropyl-2-methoxy-1-methoxymethoxy-benzene (2.0 g, 9.51 mmol) in 35 mL dry THF cooled to 0° C., BuLi (9 mL of a 1.6 m solution in hexane, 1.5 eq.) was added dropwise via a syringe and the reaction mixture was stirred 2.5 h at 0° C. This solution was then slowly added to a solution of methyl chloroformate (9 g, 95.1 mmol, 10 eq.) in 10 mL dry THF at 0° C. The mixture was stirred 12 h at r.t. Saturated KHCO3 solution and EtOAc were then added to the solution and the phases were separated. The organic layer was washed twice with saturated NaCl solution, dried over MgSO4 and evaporated in vacuo. The crude product was purified using flash chromatography (silica gel, hexane EtOAc 9:1→6:1) to yield the title compound as a yellowish oil.

後処理

  1. stirringThe mixture was stirred 12 h at r.t
  2. customthe phases were separated
  3. washThe organic layer was washed twice with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe crude product was purified

出典と根拠

ORDレコード
ord-06770eb2a49744f09793e9ad4f5a18dd
出典データセット
uspto-grants-2008_01
特許番号
US07319101B2

反応ノート

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