Water → Ethyl 3-hydroxycyclopentanecarboxylate

HRID 340773ノート

反応式

HRID 340773 の反応式
[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+].O>C1COCC1.CCOCC>[OH:11][CH:8]1[CH2:9][CH2:10][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7]1

参加物

6

反応物 3

HCID 962WaterHCID 223136Ethyl 3-oxocyclopentanecarboxylateHCID 4311764Sodium borohydride

生成物 1

HCID 53407781Ethyl 3-hydroxycyclopentanecarboxylate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of ethyl-3-oxo-cyclopentane-1-carboxylate (2.0 g) in THF (50 mL) was added NaBH4 (970 mg). The reaction mixture was maintained at 0° C. for 30 min, and then overnight at ambient temperature. The reaction was then treated with H2O and diluted with Et2O. The resulting layers were separated, and the aqueous layer was further extracted with Et2O. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting crude product (a mixture of cis/trans isomers) was used in the next step without further purification.

後処理

  1. customovernight
  2. customat ambient temperature
  3. customThe resulting layers were separated
  4. extractionthe aqueous layer was further extracted with Et2O
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionThe resulting crude product (a mixture of cis/trans isomers)
  10. customwas used in the next step without further purification

出典と根拠

ORDレコード
ord-55821370c9df45f69e38da3985873785
出典データセット
uspto-grants-2014_11
特許番号
US08895596B2

反応ノート

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