1,4-Dibromobutane → Diethyl 5-(1-cyanocyclopentyl)benzene-1,3-dioate

HRID 899459노트

반응식

HRID 899459 반응식
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:9]=1)#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH2:31][CH2:32][CH2:33][CH2:34]Br>C1COCC1>[C:1]([C:3]1([C:4]2[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1)#[N:2]

참가 물질

5

반응물 3

HCID 80561,4-DibromobutaneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 59709094Diethyl 5-(cyanomethyl)benzene-1,3-dioate

생성물 1

HCID 67318465Diethyl 5-(1-cyanocyclopentyl)benzene-1,3-dioate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of diethyl 5-(cyanomethyl)benzene-1,3-dioate (500 mg, 1.9 mmol) in 18.6 mL THF was added potassium bis(trimethylsilyl)amide (1.1 g, 5.7 mmol) and the reaction was stirred at rt for 5 min. 1,4-Dibromobutane (0.25 mL, 2.1 mmol) was added, the mixture was stirred for 45 min and then quenched with 1N HCl. Ethyl acetate was added, the layers separated and the organic layer was washed with water and brine. Drying, solvent evaporation and flash chromatography (silica gel, 0-15% EtOAc/hexanes) gave diethyl 5-(1-cyanocyclopentyl)benzene-1,3-dioate. 1H NMR (400 MHz, CDCl3) δ 8.63 (m, 1H), 8.31 (m, 2H), 4.43 (q, J=7.1 Hz, 4H), 2.56 (m, 2H), 2.14-1.99 (m, 6H), 1.43 (t, J=7.1 Hz, 6H).

후처리

  1. stirringthe mixture was stirred for 45 min
  2. customquenched with 1N HCl
  3. additionEthyl acetate was added
  4. customthe layers separated
  5. washthe organic layer was washed with water and brine
  6. customDrying
  7. customsolvent evaporation and flash chromatography (silica gel, 0-15% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-bb72fc4e9607484a98dd475c32ece0c3
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354942B2

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