HCID 15045094、化合物 → 3-(1-Methylfluoren-9-yl)propionic acid

HRID 1089853ノート

反応式

HRID 1089853 の反応式
[CH3:1][C:2]1[C:14]2[CH:13]([CH2:15][CH2:16][CH:17]3[O:21]CC[O:18]3)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.CCCCCC>CC(C)=O>[CH3:1][C:2]1[C:14]2[CH:13]([CH2:15][CH2:16][C:17]([OH:21])=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 15045094HCID 15045094、化合物HCID 21226206Ethyl acetate hexane

生成物 1

HCID 150450953-(1-Methylfluoren-9-yl)propionic acid収率 59.9%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

2-[2-(1-Methylfluoren-9-yl)ethyl]-1,3-dioxolane (4.8 g, 17.2 mmol) in 100 mL of acetone was charged slowly with John's reagent (CrO3 : H2SO4 :H2O 4:4:50 by weight) at room temperature. The reaction was monitored by TLC (silica, 10% ethyl acetate/hexane). The reaction mixture was stirred for 6 hr at room temperature, the acetone was evaporated and the residual water was extracted with ethyl acetate twice. The combined organic layers were washed with water until water became colorless. The organic solution was then extracted with 1N aqueous solution of sodium hydroxide. The basic aqueous solution was washed with ethyl acetate, acidified and extracted with ethyl acetate again. The ethyl acetate solution was dried over magnesium sulfate and evaporated. Purification of the crude by short path chromatography (silica, 25% ethyl acetate/hexane) afforded 2.6 g (59.9%) of 3-(1-methylfluoren-9-yl)propionic acid.

後処理

  1. customthe acetone was evaporated
  2. extractionthe residual water was extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with water until water
  4. extractionThe organic solution was then extracted with 1N aqueous solution of sodium hydroxide
  5. washThe basic aqueous solution was washed with ethyl acetate
  6. extractionextracted with ethyl acetate again
  7. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  8. customevaporated
  9. customPurification of the crude by short path chromatography (silica, 25% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-832c37d086984e9abaf0bb7f753c91cd
出典データセット
uspto-grants-1992_01
特許番号
US05079260

反応ノート

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