Fluorene → 2-(9H-fluoren-9-yl)ethane-1-thiol

HRID 440349

反応式

HRID 440349 の反応式
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH2:19]1[S:21][CH2:20]1>C1COCC1>[CH:1]1[C:13]2[CH:12]([CH2:19][CH2:20][SH:21])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 6853FluoreneHCID 9865ThiiraneHCID 178418339Butyllithium

生成物 1

HCID 224070292-(9H-fluoren-9-yl)ethane-1-thiol収率 68.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of fluorene (20.0 g; 120 mmol) in THF (200 mL) was cooled to -40° C. and treated with 48 mL of a 2.5M solution of n-butyllithium in hexanes (120 mmol). After stirring for 15 minutes, a solution of ethylene sulfide (6.5 mL; 109 mmol) in 30 mL of THF was added, and the resulting mixture was stirred at -40° C. for 30 minutes and room temperature for 2 hours. The reaction was quenched by the addition of saturated ammonium chloride, the layers were separated, and the organic phase was washed with 10% HCl, dried and concentrated. The crude product was purified on a flash column, eluting with hexane, to provide 16.8 g (62%) of the product as an oil that recrystallized from hexane as a white solid, mp 38°-40° C.

後処理

  1. stirringthe resulting mixture was stirred at -40° C. for 30 minutes and room temperature for 2 hours
  2. customThe reaction was quenched by the addition of saturated ammonium chloride
  3. customthe layers were separated
  4. washthe organic phase was washed with 10% HCl
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified on a flash column
  8. washeluting with hexane

出典と根拠

ORDレコード
ord-d7ae73318a8c4e7c8630bf168d4ff67b
出典データセット
uspto-grants-1996_05
特許番号
US05519043

関連ノート

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