참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Bis(2-pyridyl) ketone | HCID 88065 | — |
| 반응물 | (4-Carboxybutyl)triphenylphosphonium bromide | HCID 161236 | — |
| 반응물 | DCM MeOH AcOH | HCID 21877243 | — |
| 반응물 | Potassium tert-butoxide | HCID 23665647 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | 2-Hexenoic acid, (2E)- | HCID 5282707 | — |
| 생성물 | (Z)-Hex-2-enoic acid | HCID 12467038 | 19.8% |
반응 단계
Prepared as above from 150.0 mg (0.35 mmol) of the pyridyl ketone, 308.2 mg (0.70 mmol) of (4-carboxy-butyl)triphenylphosphonium bromide, and 1.4 mL (1.4 mmol) of 1.0 M t-BuOK in 1.5 mL of THF at 0° C. for :1.5 hr. Flash chromatography followed by preparative HPLC with MeOH-AcOH-CH2Cl2 (3.5:1.5:95) furnished 107.9 mg 60.2%) of (E)-hexenoic acid and 35.4 mg (19.8%) of (Z)-hexenoic acid (E/Z=3:1). The title (E)-isomer was characterized as follows: mp 86-90° C.; 1H NMR (CDCl3) δ8.55 (br s, 1H), 8.45 (d, J=4.7 Hz, 1H), 8.25 (s, 1H), 8.04 (d, J=8.1 Hz, 2H), 7.47 (d, J=8.0 Hz, 1H), 7.29 (d, J=8.2 Hz, 2H), 7.21 (m, 1H), 7.12 (distorted t, J=~5.1 Hz, 1H), 6.19 (t, J=7.5 Hz, 1H), 3.44 (dt, J=7.0, 6.7, Hz, 2H), 2.34 (t J=7.1 Hz, 2H), 2.25 (dt, J=7.4, 7.3 Hz, 2H), 1.68-0.82 (m, 19H); FDMS 516 (M+1). Anal. (C31H37N3O4) C, H, N.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US06031095 |
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| 출처 데이터셋 | uspto-grants-2000_02 |
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| ORD ID | ord-5f4868b847fb4fb7b21085bf149ea1cb |
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| 출처 메모 | uspto-grants-2000_02 |
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