Ammonium Chloride → 1,4a,5,7a-Tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester

HRID 1976371ノート

反応式

HRID 1976371 の反応式
[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:19][CH:18]=[C:17](C=O)[C@@H:7]2[C@H:8](OC(OCC)C)[O:9][CH:10]=1)=[O:4].C(Br)CCCC.[Mg].[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]2[CH2:19][CH:18]=[CH:17][CH:7]2[CH2:8][O:9][CH:10]=1)=[O:4]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 57167711HCID 57167711、化合物HCID 86756672Magnesium pentylbromide

生成物 1

HCID 867566711,4a,5,7a-Tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester収率 154.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

1.55 g of (1S,4aS,7aR)-1-[1-(ethoxy) ethoxy]-7-formyl-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester were dissolved in anhydrous tetrahydrofuran, followed by dropping 20 ml of magnesium pentylbromide (0.3 M tetrahydrofuran solution) while stirring and cooling at −78° C., and then stirring for 4 hours at the same temperature. After addition of saturated aqueous ammonium chloride solution to the reaction mixture, it was extracted with ethyl acetate. After washing the organic phase with brine, it was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless oil from the hexane-ether eluate in the form of (1S,4aS,7aR)-1-[1-(ethoxy) ethoxy]-7-(2-hydroxy)-n-hexyl]-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester (1.46 g, yield: 76%). The physicochemical properties of this compound are described below.

後処理

  1. stirringstirring for 4 hours at the same temperature
  2. extractionwas extracted with ethyl acetate
  3. washAfter washing the organic phase with brine, it
  4. dry with materialwas dried over magnesium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-fdd4329b137a4e65a826f98f7da5efa6
出典データセット
uspto-grants-2001_05
特許番号
US06225478B1

反応ノート

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