Triethylamine → Ethyl 3-(3-chloro-2-fluorophenyl)-2-diazo-3-oxopropanoate

HRID 242007

反応式

HRID 242007 の反応式
[Cl:1][C:2]1[C:3]([F:16])=[C:4]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.C(NC1C=CC(S([N:37]=[N+:38]=[N-])(=O)=O)=CC=1)(=O)C>C(#N)C>[Cl:1][C:2]1[C:3]([F:16])=[C:4]([C:8](=[O:15])[C:9](=[N+:37]=[N-:38])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 51291854-Acetamidobenzenesulfonyl azideHCID 64717392Ethyl 3-(3-chloro-2-fluorophenyl)-3-oxopropanoate

生成物 1

HCID 86659989Ethyl 3-(3-chloro-2-fluorophenyl)-2-diazo-3-oxopropanoate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Ethyl 3-(3-chloro-2-fluorophenyl)-3-oxopropanoate (1.30 g, 5.31 mmol), triethylamine (0.618 g, 6.11 mmol, 1.15 equiv), and 4-acetamidobenzenesulfonyl azide (1.40 g, 5.85 mmol, 1.1 equiv) were combined in acetonitrile (15 mL). After stirred at ambient temperature for 30 minutes, the mixture was concentrated in vacuo and the residue was treated with sodium hydroxide (25 mL, 2 M aqueous) and extracted with twice chloroform. The combined organic extracts were washed once with brine, dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 40:60; hexanes:ethyl acetate), providing the titled compound.

後処理

  1. concentrationthe mixture was concentrated in vacuo
  2. additionthe residue was treated with sodium hydroxide (25 mL, 2 M aqueous)
  3. extractionextracted with twice chloroform
  4. washThe combined organic extracts were washed once with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel gradient chromatography (100:0 to 40:60; hexanes:ethyl acetate)

出典と根拠

ORDレコード
ord-85b62a5695854a139211369c4df8ff2b
出典データセット
uspto-grants-2014_02
特許番号
US08653079B2

関連ノート

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