Ammonium Chloride → 3,3-Dimethyl-1-[2-benzylperhydropyridazinyl]pentane-1,2-dione

HRID 851944ノート

反応式

HRID 851944 の反応式
[O:1]=[C:2]([CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][N:8]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5]C)=O.[CH3:20][C:21]([Mg]Cl)([CH3:24])[CH2:22][CH3:23].[Cl-].[NH4+]>C1COCC1>[CH3:20][C:21]([CH3:24])([CH2:22][CH3:23])[C:3](=[O:5])[C:2]([CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][N:8]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:1]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 18470067Methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetateHCID 178446075HCID 178446075、化合物

生成物 1

HCID 184700773,3-Dimethyl-1-[2-benzylperhydropyridazinyl]pentane-1,2-dione収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetate (9.0 g, 29.4 mmol) in 30 ml dry THF was cooled to −78° C. and treated with 35 ml of 1.0 M solution of 1,1-dimethylpropylmagnesium chloride in THF. After stirring the resulting homogeneous mixture at for 5 hours, the mixture was poured into saturated ammonium chloride (150 ml) and extracted into ethyl acetate. The organic layer was washed with water, dried and concentrated. The crude material was purified by silica gel column, eluting with 10% ethyl acetate in hexane, to obtain 7.0 g product (69% yield) as clear oil. 1H NMR (CDCl3, 400 MHz): δ 0.76 (t, 3H, J=7.0); 1.06 (s, 6H) 1.69 (m, 6H); 2.80 (m, 1H); 3.15 (m, 1H), 4.03 (m, 1H); 4.13 (m, 1H), 5.18 (m, 2H), 7.36 (m, 5H).

後処理

  1. extractionextracted into ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel column
  6. washeluting with 10% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-5b7e5302d9f94c2391f5b08c3cbff002
出典データセット
uspto-grants-2007_08
特許番号
US07253169B2

反応ノート

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