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Calcium Carbonate → 2-(1-Phenylcyclopentyl)acetaldehyde

HRID 1734905
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HRID 1734905 반응식
[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
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참가 물질

6

반응물 2

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

생성물 1

HCID 199660432-(1-Phenylcyclopentyl)acetaldehyde수율 96%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eaccc944365d408a8dcb9f0c30a59d64
출처 데이터셋
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05534529

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