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

HRID 1786565ノート

反応式

HRID 1786565 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-dd218db336c3408d83fea32600257830
出典データセット
uspto-grants-2009_03
特許番号
US07507754B2

反応ノート

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