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Iodoethane → 3-Ethyl-3-(3-methoxyphenyl)azepan-2-one

HRID 429067
ノート
印刷プレビュー

反応式

HRID 429067 の反応式
[Li][CH2:2][CH2:3][CH2:4][CH3:5].CCCCCC.CC1(C)CCCC(C)(C)N1.C[Si](C)(C)[N:24]1[CH2:30][CH2:29][CH2:28][CH2:27]C[C:25]1=[O:31].Cl[C:35]1[CH:40]=[CH:39]C=[CH:37][C:36]=1[O:41][CH3:42].C(I)C>C1COCC1>[CH2:4]([C:3]1([C:2]2[CH:39]=[CH:40][CH:35]=[C:36]([O:41][CH3:42])[CH:37]=2)[CH2:27][CH2:28][CH2:29][CH2:30][NH:24][C:25]1=[O:31])[CH3:5]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 6

HCID 6340IodoethaneHCID 8058Hexane2 回HCID 130112-ChloroanisoleHCID 130352,2,6,6-TetramethylpiperidineHCID 114239991-Trimethylsilanyl-azepan-2-oneHCID 178418339Butyllithium2 回

生成物 1

HCID 2815455
3-Ethyl-3-(3-methoxyphenyl)azepan-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To 1.6 M n-BuLi in hexane (31.3 mL, 50 mmol) at 0° C. was added a solution of 2,2,6,6-tetramethyl piperidine (8.43 mL, 50 mmol) in anhydrous THF (100 mL) over 5 min. 1-Trimethylsilanyl-azepan-2-one (as described in Step F above) (9.26 g, 50 mmol) in anhydrous THF (20 mL) was added. After stirring the reaction mixture for 10 min, a further portion of 1.6M n-BuLi in hexane (31.3 mL, 50 mmol) was added, the mixture stirred for 10 min, and 2-chloroanisole (6.34 mL, 50 mmol) was added. After stirring for 30 min under Ar, ethyl iodide (3.90 mL, 48.7 mmol) was added, the reaction mixture was stirred for 30 min, quenched with H2O, concentrated in vacuo, diluted with EtOAc, and washed with 5N HCl (100 mL) and brine. The organic layer was dried (MgSO4), concentrated and purified using SiO2 chromatography (10-15% EtOAc/CH2Cl2) to give the title compound

後処理

  1. stirringthe mixture stirred for 10 min
  2. additionwas added
  3. stirringthe reaction mixture was stirred for 30 min
  4. customquenched with H2O
  5. concentrationconcentrated in vacuo
  6. additiondiluted with EtOAc
  7. washwashed with 5N HCl (100 mL) and brine
  8. dry with materialThe organic layer was dried (MgSO4)
  9. concentrationconcentrated
  10. custompurified

出典と根拠

ORDレコード
ord-382a25474c234a80afc519e85113c9d9
出典データセット
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06316436B1

反応ノート

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