Benzyl Alcohol → HCID 15725027、化合物

HRID 846673ノート

反応式

HRID 846673 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[S:10][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:15])[C:12]([OH:14])=[O:13].N(C(OCC)=O)=NC(OCC)=O.[CH2:34](O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[S:10][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:15])[C:12]([O:14][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:13]

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15724967HCID 15724967、化合物

生成物 1

HCID 15725027HCID 15725027、化合物収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution (5 ml) of 2-(1H-indol-2-yl)thio-2-phenylpropionic acid (1.5 g) and diethyl azodicarboxylate (0.96 g) in anhydrous tetrahydrofuran, a solution (5 ml) of benzyl alcohol (0.81 g) and triphenylphoshine (1.44 g) in anhydrous tetrahydrofuran was added dropwise under an argon atmosphere, and the mixture was stirred at room temperature overnight. The solvent was evaporated off under reduced pressure. Benzene was added to the residue, and deposited crystalline matter was filtered and the solvent was evaporated. The residue was purified by silica gel column chromatography (diluting solvent: n-hexane/ethyl acetate=9:1), and was further recrystallized from ethyl acetate/n-hexane to give 1.37 g (yield 71 %) of the product compound as a colorless scale-like crystal. The melting point was 102°-103° C.

後処理

  1. customThe solvent was evaporated off under reduced pressure
  2. additionBenzene was added to the residue
  3. filtrationwas filtered
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (diluting solvent: n-hexane/ethyl acetate=9:1)
  6. customwas further recrystallized from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-d4b11bd418b743d8893744335ad63d8a
出典データセット
uspto-grants-1992_08
特許番号
US05137909

反応ノート

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