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

HRID 899459ノート

反応式

HRID 899459 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bb72fc4e9607484a98dd475c32ece0c3
出典データセット
uspto-grants-2008_04
特許番号
US07354942B2

反応ノート

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