N-methyl-2-pyrrolidone → 4-(Heptyloxy)benzonitrile

HRID 1622980ノート

反応式

HRID 1622980 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.[CH3:16][N:17]1C(=O)CCC1>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]#[N:17])=[CH:3][CH:4]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

参加物

5

反応物 2

HCID 13387N-methyl-2-pyrrolidoneHCID 5991021-(4-Bromophenoxy)heptane

生成物 1

HCID 52310344-(Heptyloxy)benzonitrile収率 73%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
100 °C

実験手順

Prepared using General Procedure 1: A stirred a solution of 1-bromo-4-(heptyloxy)benzene (2.0 g, 7.37 mmol), zinc cyanide (1.73 g, 14.74 mmol) and tetrakis(triphenylphosphine)palladium (76.12 mg, 0.07 mol) in dry NMP (20 mL) was degassed with N2. The reaction was heated to 100° C. for 18 h while stirring under nitrogen. The reaction mixture was cooled and poured into water (100 mL) and DCM (20 mL). The solid material was removed by filtration and the filtrate was extracted with water (3×20 mL). The organic layer was dried over MgSO4 and concentrated. The crude product was purified by chromatography (EA/hexanes) to afford 1.15 g (73%) of 4-(heptyloxy)benzonitrile as a light yellow solid. LCMS-ESI (m/z) calculated for C14H19NO: 217.1; found 218.1 [M+H]+, tR=11.14 min (Method 2). 1H NMR (400 MHz, CDCl3) δ 7.64-7.50 (m, 2H), 7.05-6.83 (m, 2H), 3.99 (t, J=6.5 Hz, 2H), 1.89-1.69 (m, 2H), 1.58-1.12 (m, 8H), 0.90 (dd, J=9.1, 4.5 Hz, 3H). 13C NMR (101 MHz CDCl3) δ 162.47, 133.91, 132.78, 132.12, 129.13, 119.31, 115.18, 103.58, 68.41, 31.73, 28.98, 25.89, 22.58, 14.07.

後処理

  1. customPrepared
  2. customwas degassed with N2
  3. temperatureThe reaction mixture was cooled
  4. additionpoured into water (100 mL) and DCM (20 mL)
  5. customThe solid material was removed by filtration
  6. extractionthe filtrate was extracted with water (3×20 mL)
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated
  9. customThe crude product was purified by chromatography (EA/hexanes)

出典と根拠

ORDレコード
ord-51dbb871e4fb44e5a36db010f540897f
出典データセット
uspto-grants-2014_07
特許番号
US08778923B2

反応ノート

読み込み中…