Ethyl diazoacetate → HCID 53959852、化合物

HRID 567708ノート

反応式

HRID 567708 の反応式
[Cl:1][C:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]=1[C:9](Cl)=[O:10].[N+:12](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N-:13].CC1(C)CCCC(C)(C)N1.[Li]>C1COCC1>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[N+:12]=[N-:13])[C:9]([C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:2]=1[Cl:1])=[O:10])[CH3:19]

参加物

5

反応物 3

HCID 12192Ethyl diazoacetateHCID 212625662-Chlorocyclohept-1-ene-1-carbonyl chlorideHCID 57419888piperidine, 2,2,6,6-tetramethyl-, lithium salt

生成物 1

HCID 53959852HCID 53959852、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-chlorocyclohept-1-enecarbonyl chloride (4.6 g) and ethyl diazoacetate (2.8 ml) in THF (30 ml) cooled to −70C was added a solution of lithium 2,2,6,6-tetramethylpiperidine (1 equiv.) dropwise. On completion of the addition the reaction mixture was stirred for 1 h. The reaction mixture was quenched by pouring into 1M citric acid (100 ml), then extracted with ether (3×200 ml). The ether extracts were combined, washed with brine, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil. The oil was purified by flash chromatography using a gradient elution: hexane/ether (10:1) 500 ml, hexane/ether (9:1) 500 ml, hexane/ether (8:2) 500 ml. The appropriate fractions were combined and evaporated under reduced pressure to give a yellow oil. δH (360 MHz; CDCl3) 1.33 (3H, t, J=7 Hz, CH3), 1.74 (6H, m, CH2), 2.32 (2H, m, CH2), 2.64 (2H, m, CH2), 4.29 (2H, t, J=7 Hz, CH2).

後処理

  1. additionOn completion of the addition the reaction mixture
  2. customThe reaction mixture was quenched
  3. additionby pouring into 1M citric acid (100 ml)
  4. extractionextracted with ether (3×200 ml)
  5. washwashed with brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto give an oil
  10. customThe oil was purified by flash chromatography
  11. washa gradient elution
  12. customevaporated under reduced pressure
  13. customto give a yellow oil

出典と根拠

ORDレコード
ord-63255e2c5df9476b931ca259708c0104
出典データセット
uspto-grants-2001_01
特許番号
US06180630B2

反応ノート

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