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Calcium Carbonate → 2-(1-Phenylcyclopentyl)acetaldehyde

HRID 1734905
ノート
印刷プレビュー

反応式

HRID 1734905 の反応式
[C:1](=[O:4])([O-])[O-].[Ca+2].[C:6]1([C:12]2([CH2:17]C3SCCCS3)[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(#N)C.O.C(OCC)(=O)C>[C:6]1([C:12]2([CH2:17][CH:1]=[O:4])[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=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

6

反応物 2

HCID 10112Calcium CarbonateHCID 199661182-(1-Phenylcyclopentyl)methyl-1,3-dithiane

生成物 1

HCID 199660432-(1-Phenylcyclopentyl)acetaldehyde収率 96%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

263 mg (0.969 mmol) of mercuric chloride and 129 mg (1.29 mmol) of calcium carbonate were added to a suspension of 90 mg (0.323 mmol) of 2-(1-phenylcyclopentyl)methyl-1,3-dithiane [prepared as described in step (iv) above] in a mixture of 4 ml of acetonitrile and 0.6 ml of water, and the resulting mixture was stirred for 3 hours at 90° C. At the end of this time, the reaction mixture was cooled and then diluted with ethyl acetate. The insoluble materials were filtered off from the diluted mixture with the help of Celite (trade mark) filter aid. The filtrate was then washed with a 1M aqueous solution of sodium acetate, with a saturated aqueous solution of ammonium chloride and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 5 g of silica gel, using methylene chloride as the eluent, to give 58.4 mg (yield 96%) of the title compound as a foam-like material.

後処理

  1. temperatureAt the end of this time, the reaction mixture was cooled
  2. filtrationThe insoluble materials were filtered off from the diluted mixture with the help of Celite (trade mark)
  3. filtrationfilter aid
  4. washThe filtrate was then washed with a 1M aqueous solution of sodium acetate, with a saturated aqueous solution of ammonium chloride and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through 5 g of silica gel

出典と根拠

ORDレコード
ord-eaccc944365d408a8dcb9f0c30a59d64
出典データセット
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05534529

反応ノート

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