Tetrabutylammonium Fluoride → (4-Hydroxymethyl-5-methyl-furan-2-yl)-acetic acid ethyl ester

HRID 1786575ノート

反応式

HRID 1786575 の反応式
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[O:7][C:8]([CH3:23])=[C:9]([CH2:11][O:12][Si](C(C)C)(C(C)C)C(C)C)[CH:10]=1)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[O:7][C:8]([CH3:23])=[C:9]([CH2:11][OH:12])[CH:10]=1)[CH3:2]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 58824185(5-Methyl-4-triisopropylsilanyloxymethyl-furan-2-yl)-acetic acid ethyl ester

生成物 1

HCID 58824186(4-Hydroxymethyl-5-methyl-furan-2-yl)-acetic acid ethyl ester収率 67.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (5-methyl-4-triisopropylsilanyloxymethyl-furan-2-yl)-acetic acid ethyl ester (29) (0.5 g) in tetrahydrofuran (3.0 mL) was cooled to 0° C. with stirring and treated with tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 2.82 mL) under argon. After 30 minutes, the resulting solution was concentrated in-vacuo and partitioned between water (30 mL) and ethyl acetate (4×25 mL). The combined organic extracts were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting with diethyl ether/petroleum ether (1:1 by volume) to give compound 30 as a clear oil (188 mg). LC/MS System A: Rt=2.34 mins.

後処理

  1. concentrationthe resulting solution was concentrated in-vacuo
  2. custompartitioned between water (30 mL) and ethyl acetate (4×25 mL)
  3. washThe combined organic extracts were washed with brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with diethyl ether/petroleum ether (1:1 by volume)

出典と根拠

ORDレコード
ord-8d40e02461f94836b554b430ff35d267
出典データセット
uspto-grants-2009_03
特許番号
US07507754B2

反応ノート

読み込み中…