Ethyl Acetate → HCID 67469173、化合物

HRID 1019758ノート

反応式

HRID 1019758 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13][C:14](OC)=[O:15].[Li+].[BH4-].[NH4+].[Cl-].CCOC(C)=O>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13][CH2:14][OH:15]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 67468998HCID 67468998、化合物

生成物 1

HCID 67469173HCID 67469173、化合物収率 72.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Methyl 2-(2-chloro-5-methoxy-4-nitrophenyl)acetate (10.2 g, 41.86 mmol) was dissolved in dry THF (200 mL) and cooled to 0° C. A 2M solution of LiBH4 in THF (41.86 mL, 83.73 mmol) was added at 0° C. over 20 minutes then the mixture was allowed to warm to room temperature and stirred for 5 hours. Saturated NH4Cl solution was added to the reaction cautiously and stirred further for 15 minutes then EtOAc (150 mL) and water (150 mL) were added. The separated aqueous phase was extracted with EtOAc (100 mL) then the combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 0-2% methanol in DCM to give the title compound (7.0 g, 72%) as a solid.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred further for 15 minutes
  3. extractionThe separated aqueous phase was extracted with EtOAc (100 mL)
  4. dry with materialthe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on neutral silica gel using 0-2% methanol in DCM

出典と根拠

ORDレコード
ord-58e00c8296a94496a762a8edf590a6d1
出典データセット
uspto-grants-2014_05
特許番号
US08716287B2

反応ノート

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