Lithium hydroxide, monohydrate → 4-(4-Chlorophenyl)-4-(methoxyimino)butanoic acid

HRID 423072ノート

反応式

HRID 423072 の反応式
O.[OH-].[Li+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:19][O:20][CH3:21])[CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[CH:7][CH:6]=1>O.C1COCC1.C(O)C.CCOC(C)=O>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:19][O:20][CH3:21])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:7][CH:6]=1

参加物

7

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 86632052Ethyl 4-(4-chlorophenyl)-4-(methoxyimino)butanoate2 回

生成物 1

HCID 866320534-(4-Chlorophenyl)-4-(methoxyimino)butanoic acid収率 69.1%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

Lithium hydroxide monohydrate (9.59 g, 228.57 mmol) was added to ethyl 4-(4-chlorophenyl)-4-(methoxyimino)butanoate (Intermediate 52) (12.33 g, 45.71 mmol) in water (25.4 mL), THF (102 mL) and ethanol (102 mL). The resulting solution was stirred at 20° C. for 1 day. The reaction mixture was diluted with EtOAc (200 mL) and washed with water (200 mL). The aqueous was adjusted to pH5 with 1M citric acid solution then extracted with EtOAc (3×150 mL). The organic extracts were washed with saturated brine (25 mL) then dried over MgSO4, filtered and evaporated to afford desired product 4-(4-chlorophenyl)-4-(methoxyimino)butanoic acid (7.63 g, 69.1%) as a light yellow solid.

後処理

  1. washwashed with water (200 mL)
  2. extractionthen extracted with EtOAc (3×150 mL)
  3. washThe organic extracts were washed with saturated brine (25 mL)
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-c558eee4cfbc47ab816ab9469084dc81
出典データセット
uspto-grants-2012_01
特許番号
US08101623B2

反応ノート

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