Methyl chloroformate → 5-Methyl-4-triisopropylsilanyloxymethyl-furan-2-carboxylic acid methyl ester

HRID 460039ノート

反応式

HRID 460039 の反応式
[CH:1]([Si:4]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[O:5][CH2:6][C:7]1[CH:11]=[CH:10][O:9][C:8]=1[CH3:12])([CH3:3])[CH3:2].C([Li])(CC)C.Cl[C:25]([O:27][CH3:28])=[O:26].[Cl-].[NH4+]>O1CCCC1>[CH3:28][O:27][C:25]([C:10]1[O:9][C:8]([CH3:12])=[C:7]([CH2:6][O:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:13]([CH3:15])[CH3:14])[CH:16]([CH3:18])[CH3:17])[CH:11]=1)=[O:26]

参加物

6

反応物 4

HCID 6586Methyl chloroformateHCID 25517Ammonium ChlorideHCID 11043781Silane, tris(1-methylethyl)[(2-methyl-3-furanyl)methoxy]-HCID 178418400CID 53628100

生成物 1

HCID 588242025-Methyl-4-triisopropylsilanyloxymethyl-furan-2-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (10.0 g) in tetrahydrofuran (300 mL) was cooled to −78° C. with stirring was treated drop-wise with sec-butyllithium (3.0 M in cyclohexane, 37 mL). After 1 hour the reaction mixture was treated drop-wise with a solution of methyl chloroformate (5.2 g) in tetrahydrofuran (30 mL) over 10 mins and stirring was continued at −78° C. for 1 hour. The reaction mixture was then treated with saturated ammonium chloride solution (300 mL) and allowed to warm to ambient temperature. The two layers were separated and the organic phase washed with brine (300 mL), dried and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate/pentane (1:9 by volume) to give compound 15 as a clear oil.

後処理

  1. stirringstirring
  2. customThe two layers were separated
  3. washthe organic phase washed with brine (300 mL)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethyl acetate/pentane (1:9 by volume)

出典と根拠

ORDレコード
ord-7d3f5da89a88434d8c988b0287a11a5a
出典データセット
uspto-grants-2007_03
特許番号
US07196089B2

反応ノート

読み込み中…