Dimethylformamide → N,N-Dimethyl-2-[2-(2-naphthyl)ethenyloxy]ethanamine

HRID 368913

反応式

HRID 368913 の反応式
O([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)S(C(F)(F)F)(=O)=O.[CH3:19][N:20]([CH3:26])[CH2:21][CH2:22][O:23][CH:24]=[CH2:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C=O)C>CCCCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:19][N:20]([CH3:26])[CH2:21][CH2:22][O:23][CH:24]=[CH:25][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 19240Dimethylaminoethyl vinyl etherHCID 45463412-Naphthyl Trifluoromethanesulfonate

生成物 1

HCID 54382846N,N-Dimethyl-2-[2-(2-naphthyl)ethenyloxy]ethanamine収率 87%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8003Pentane溶媒

実験手順

Table 1, Entry 7. In the reaction tube were mixed 2-naphthyl triflate (0.276 g, 1.0 mmol), [2-(dimethylamino)ethoxy]ethene (0.23 g, 2.0 mmol), palladium acetate (0.00673 g, 0.030 mmol), triphenylphosphine (0.0173 g, 0.066 mmol) triethylamine (0.202 g, 2.0 mmol) and 0.75 ml DMF.under nitrogen. The contents of the flask were irradiated for 7.00 min with an effect of 35 W. After cooling, the product mixture was diluted with 50 ml pentane, transferred to a separatory funnel and washed with 2×25 ml water. Additional extraction of the aqueous phases was performed with 25 ml pentane. The combined organic portions were then treated 5 times with 20 ml of 0.1 M HCl. The aqueous extracts were combined, poured into a flask containing excess NaOH (1.0 M) and was extracted with 2×50 ml pentane. The combined organic phases were dried (K2CO3) and concentrated by evaporation. The yield was 87% (yellow oil, trans/cis 1/1).

後処理

  1. customThe contents of the flask were irradiated for 7.00 min with an effect of 35 W
  2. temperatureAfter cooling
  3. customtransferred to a separatory funnel
  4. washwashed with 2×25 ml water
  5. extractionAdditional extraction of the aqueous phases
  6. additionThe combined organic portions were then treated 5 times with 20 ml of 0.1 M HCl
  7. additionpoured into a flask
  8. additioncontaining excess NaOH (1.0 M)
  9. extractionwas extracted with 2×50 ml pentane
  10. dry with materialThe combined organic phases were dried (K2CO3)
  11. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-270971c7c18d412cbbc9a60a2c91ba80
出典データセット
uspto-grants-2000_10
特許番号
US06136157

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