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

HRID 851944노트

반응식

HRID 851944 반응식
[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]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 18470067Methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetateHCID 178446075HCID 178446075, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5b7e5302d9f94c2391f5b08c3cbff002
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253169B2

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