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Ethyl Acetate → Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-vinylfuran-3-yl)-benzoate

HRID 1778351
ノート
印刷プレビュー

反応式

HRID 1778351 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]1([S:17]([CH2:20][C:21]2[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([OH:31])[C:24]([C:32]3[CH:36]=[CH:35][O:34][C:33]=3[CH:37]=O)=[CH:23][CH:22]=2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:39](OCC)(=O)C.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:11]1([S:17]([CH2:20][C:21]2[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([OH:31])[C:24]([C:32]3[CH:36]=[CH:35][O:34][C:33]=3[CH:37]=[CH2:39])=[CH:23][CH:22]=2)(=[O:19])=[O:18])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86684730Methyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate2 回

生成物 1

HCID 66685753Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-vinylfuran-3-yl)-benzoate

試薬・触媒・溶媒 2

HCID 74505
Methyltriphenyliphosphonium bromide
触媒
HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

A suspension of methyltriphenylphosphonium bromide (pre-dried under vacuum at 60° C., 3.80 g) in THF (60 mL) was cooled to 5° C., under nitrogen. Potassium bis-(trimethylsilyl)amide (0.5M in toluene, 21.3 mL) was added and the suspension was warmed to room temperature and stirred for 45 minutes. It was cooled to −78° C. and a solution of methyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate (Intermediate 28, 1.42 g) in THF (40 mL) was added and the mixture was warmed to room temperature and stirred for 2.5 hours. Ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the mixture and the organic layer was separated, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-35% to give methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-vinylfuran-3-yl)-benzoate (1.24 g) as a white solid.

後処理

  1. temperaturethe suspension was warmed to room temperature
  2. temperatureIt was cooled to −78° C.
  3. temperaturethe mixture was warmed to room temperature
  4. stirringstirred for 2.5 hours
  5. customthe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was purified by chromatography on silica
  11. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-35%

出典と根拠

ORDレコード
ord-b6507285499f4280a0aa9ff34b0cf0e3
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266896B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート