Tetrahydrofuran → Ethyl 4-(3-(naphthalen-2-yl)propanamido)benzoate

HRID 2422946ノート

反応式

HRID 2422946 の反応式
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:12][C:13]([NH:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)=[O:14].C1COCC1>CO.Cl[Ni]Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=1)=[O:14]

参加物

5

反応物 2

HCID 8028TetrahydrofuranHCID 67243223Ethyl 4-(3-naphthalen-2-yl-acryloylamino)benzoate

生成物 1

HCID 24782383Ethyl 4-(3-(naphthalen-2-yl)propanamido)benzoate収率 79%

試薬・触媒・溶媒 2

HCID 24385Nickel Dichloride触媒HCID 887Methanol溶媒

実験手順

Ref. J. of Org. Chem., 2000, 65, 8001. To a stirred solution of amide 42 (0.086 g, 0.249 mmol) and NiCl2 6H2O (0.118 g, 0.498 mmol, 2 eq) in methanol (8 ml) and THF (4 ml) NaBH4 (0.028 g, 0.749 mmol, 4 eq) was added portionwise over 20 min at 0° C. After stirring for 1 h at room temperature, the solvent was distilled off under reduced pressure. Water (10 ml) and ethyl acetate (10 ml) was added. The resulting mixture was filtered through a celite bed which was washed with ethyl acetate (20 ml). After collecting the filtrate, the organic phase was separated, dried over Na2SO4 and the solvent was distilled off under reduced pressure to give the pure product 69 as a white solid (0.066 g, 0.190 mmol, 79%), mp 119-121° C. 1H NMR (400 MHz, CDCl3) δ 1.38 (3H, t, J 7.2 Hz, CH2CH3) 2.75 (2H, t, J 7.2 Hz, CH2CO), 3.23 (2H, t, J 7.2 Hz, CH2—Ar), 4.35 (2H, q, J 7.2 Hz, CH2CH3), 7.12 (1H, bs, N—H), 7.37 (1H, dd, J 1.6, 8.4 Hz, CH, Ar), 7.42-7.50 (4H, m, 4×CH, Ar), 7.69 (1H, bs, CH, Ar), 7.76-7.82 (3H, m, 3×CH, Ar), 7.97 (2H, d, J 9.2 Hz, 2×CH, Ar). MS (API-ES): m/z 348 [M+H]+ (100%), HRMS (API-ES) m/z found 348.1602 [M+H]+.

後処理

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionWater (10 ml) and ethyl acetate (10 ml) was added
  3. filtrationThe resulting mixture was filtered through a celite bed which
  4. washwas washed with ethyl acetate (20 ml)
  5. customAfter collecting the filtrate
  6. customthe organic phase was separated
  7. dry with materialdried over Na2SO4
  8. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-9b53b3bc347f41958ca4f2bbeb78fdd6
出典データセット
uspto-grants-2011_06
特許番号
US07960434B2

反応ノート

読み込み中…