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Diethyl Ether → HCID 9910901, 화합물

HRID 1740880
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HRID 1740880 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1.CCOCC>C(COC)OC.CO>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:34]([C:33]3[CH:36]=[CH:37][C:30]([F:29])=[CH:31][CH:32]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[S:15]2(=[O:17])=[O:16])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 680234-FluorobenzaldehydeHCID 1237760HCID 1237760, 화합물HCID 178418339Butyllithium

생성물 1

HCID 9910901HCID 9910901, 화합물수율 46%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 8071
1,2-Dimethoxyethane
용매
2회

실험 절차

A solution of N-(l-benzylpiperidin-4-yl)benzenesulfonamide from Example 1 above, (18.7 g, 56.5 mmol) and 210 ml dimethoxyethane was chilled at 0° C. under N2, followed by a slow addition over 25 minutes of 2.3 equivalent of n-butyl lithium (52 ml, 2.5 N/hexanes, 130 mmol) keeping the temperature below 15° C. After mechanically stirring for 35 minutes longer, 4-fluorobenzaldehyde (7.4 g, 59 mmol) in 50 ml dimethoxyethane was added at 5° C., and the reaction was stirred for 2 hours. Ether (400 ml) was added, and the reaction was washed with water and brine, dried (MgSO4), and concentrated in vacuo. The residue was chromatographed on silica gel eluting with CHCl3 to CHCl3 :5% MeOH to afford 11.85 g (46% yield) of the intermediate as a foam.

후처리

  1. customthe temperature below 15° C
  2. stirringthe reaction was stirred for 2 hours
  3. washthe reaction was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with CHCl3 to CHCl3

출처 및 근거

ORD 기록
ord-11df61dcfa1441e0aa789456c557c498
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05972963

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