Sodium borohydride → 4-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl ester

HRID 1429190ノート

反応式

HRID 1429190 の反応式
[BH4-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[CH2:11][C:10](=[O:12])[CH:9]=[C:8]1[C:13]([O:15][CH3:16])=[O:14])=[O:6]>CO>[CH3:16][O:15][C:13]([CH:8]1[CH2:9][CH:10]([OH:12])[CH:11]=[C:7]1[C:5]([O:4][CH3:3])=[O:6])=[O:14]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 591654631,2-Dimethyl 4-oxo-2-cyclopentene-1,2-dicarboxylate

生成物 1

HCID 591654434-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl ester収率 93.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

NaBH4 (0.66 g, 17.5 mmol) dissolved in MeOH (23 mL) was added to a cold solution (−30° C.) of the ketone 23a (3.18 g, 16.1 mmol). After nine minutes the excess of NaBH4 was destroyed by adding brine (80 mL). The mixture was concentrated and extracted with ethyl acetate (4×80 ml). The organic phases were dried, filtrated and concentrated which gave the title compound (3.0 g, 92%) as a yellow oil.

後処理

  1. customAfter nine minutes the excess of NaBH4 was destroyed
  2. additionby adding brine (80 mL)
  3. concentrationThe mixture was concentrated
  4. extractionextracted with ethyl acetate (4×80 ml)
  5. customThe organic phases were dried
  6. filtrationfiltrated
  7. concentrationconcentrated which

出典と根拠

ORDレコード
ord-12facf2eb21845baa7e9cba33c1b1533
出典データセット
uspto-grants-2015_01
特許番号
US08937080B2

反応ノート

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