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Sodium Hydroxide → HCID 15410800、化合物

HRID 1075469
ノート
印刷プレビュー

反応式

HRID 1075469 の反応式
[CH2:1]([S:8][CH2:9][CH:10]([CH2:21][CH2:22][C:23]([O:25]CC1C=CC=CC=1)=[O:24])[C:11]([O:13]CC1C=CC=CC=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[CH2:1]([S:8][CH2:9][CH:10]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 15410799Dibenzyl 2-[(benzylsulfanyl)methyl]pentanedioate

生成物 1

HCID 15410800HCID 15410800、化合物収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cooled solution (5° C.) of dibenzyl 2-[(benzylsulfanyl)methyl]pentanedioate (15.29 g, 33.9 mmol) in tetrahydrofuran (750 ml) was added 0.1 N NaOH (745 ml, 74.5 mmol NaOH) with stirring. The cloudy reaction mixture was allowed to warm to room temperature. After 16 hours, the reaction mixture had become homogenous. The solution was concentrated under reduced pressure to remove the tetrahydrofuran. The remaining aqueous solution was washed with ethyl acetate, then made acidic (pH 1) with concentrated HCl. The mixture was extracted twice with ethyl acetate. The ethyl acetate was removed under reduced pressure and the resulting waxy solid was purified by column chromatography to yield 6.9 g (76%) of white solid. 1H NMR (d6-DMSO): δ 1.7 (m, 2H), 2.2 (t, 2H), 2.3-2.6 (m, 3H), 3.8 (s, 2H), 7.3 (s, 5H).

後処理

  1. customThe cloudy reaction mixture
  2. concentrationThe solution was concentrated under reduced pressure
  3. customto remove the tetrahydrofuran
  4. washThe remaining aqueous solution was washed with ethyl acetate
  5. extractionThe mixture was extracted twice with ethyl acetate
  6. customThe ethyl acetate was removed under reduced pressure
  7. customthe resulting waxy solid was purified by column chromatography

出典と根拠

ORDレコード
ord-f537b7e3d2f344b5bba9f21e85cbadfe
出典データセット
uspto-grants-1999_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05902817

反応ノート

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