Dimethylformamide → (E)-methyl 3-(4-((2-formyl-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate

HRID 632664노트

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HRID 632664 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=3)=[CH:9][S:8][C:7]=2[CH:24]=1.O=P(Cl)(Cl)Cl.CN([CH:33]=[O:34])C>C(Cl)(Cl)Cl>[CH:33]([C:9]1[S:8][C:7]2[CH:24]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=1)=[O:34]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 86730639(E)-methyl 3-(4-((6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate

생성물 1

HCID 118574925(E)-methyl 3-(4-((2-formyl-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate수율 95.5%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
0 °C

실험 절차

To a solution of (E)-methyl 3-(4-((6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (30 mg, 0.088 mmol) in CHCl3 (1.5 mL) at 0° C. was added POCl3 (0.5 mL, 5.36 mmol) followed by DMF (0.5 mL, 6.46 mmol). The resulting mixture was stirred at 0° C. for 5 min and then allowed to warm to room temperature for 2 h after which time the reaction was again cooled to 0° C. and quenched by dropwise addition of water. The mixture was then partitioned between 1N aqueous NaOH and CH2Cl2. The layers were separated and the organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford (E)-methyl 3-(4-((2-formyl-6-methoxybenzo[b]thiophen-3-yl)oxy)phenyl)acrylate (31 mg, 0.084 mmol, 95% yield) which was used without further purification. LC/MS (m/z, MH+): 369.0.

후처리

  1. temperatureto warm to room temperature for 2 h after which time the reaction
  2. temperaturewas again cooled to 0° C.
  3. customquenched by dropwise addition of water
  4. customThe mixture was then partitioned between 1N aqueous NaOH and CH2Cl2
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-79e5838e46b04b40a028746c837dae1d
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321746B2

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