Dimethylformamide → tert-Butyl 3-(3-cyanophenethoxy)propanoate

HRID 909899ノート

反応式

HRID 909899 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH3:20][N:21](C=O)C>C(OCC)(=O)C.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.[C-]#N.[Zn+2].[C-]#N>[C:20]([C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])#[N:21]

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 67075913tert-Butyl 3-(3-bromophenethoxy)propanoate

生成物 1

HCID 58168561tert-Butyl 3-(3-cyanophenethoxy)propanoate

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

Pd(Ph3P)4 (0.53 g) was added in one portion to tert-butyl 3-(3-bromophenethoxy)propanoate [Preparation 3, Step i)] (3.00 g), and zinc cyanide (1.68 g) in DMF (35 mL) under nitrogen. The resulting mixture was stirred at 130° C. for 30 min. The reaction mixture was diluted with ethyl acetate (100 mL) and filtered through Celite. Isohexane (100 mL) was added and the mixture was washed with water (4×20 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0-20% ethyl acetate in isohexane to afford the subtitled compound (2.30 g). 1H NMR (300 MHz, CDCl3) δ 7.54-7.43 (m, 3H), 7.41-7.34 (m, 1H), 3.67 (t, J=6.3 Hz, 2H), 3.66 (t, J=6.6 Hz, 2H), 2.89 (t, J=6.5 Hz, 2H), 2.47 (t, J=6.3 Hz, 2H), 1.43 (s, 9H).

後処理

  1. filtrationfiltered through Celite
  2. additionIsohexane (100 mL) was added
  3. washthe mixture was washed with water (4×20 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford crude product
  8. customThe crude product was purified by flash silica chromatography, elution gradient 0-20% ethyl acetate in isohexane

出典と根拠

ORDレコード
ord-56b794228eee4ba984bce8d8ee347465
出典データセット
uspto-grants-2011_09
特許番号
US08017602B2

反応ノート

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