Ethyl 4-iodobenzoate → (E)-ethyl 4-styrylbenzoate

HRID 533715노트

반응식

HRID 533715 반응식
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH:13](/B(O)O)=[CH:14]\[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH:13](/[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1)=[CH:14]\[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

4

반응물 2

HCID 142891Ethyl 4-iodobenzoateHCID 5702628Styrylboronic acid

생성물 1

HCID 5907907(E)-ethyl 4-styrylbenzoate수율 85%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
160 °C

실험 절차

To a solution of ethyl 4-iodobenzoate (1.0 g, 3.6 mmol) in DMF (4 mL) was added commercial (E)-styrylboronic acid (538 mg, 3.6 mmol) and catalytic Pd(tBuP)2. The reaction vessel was sealed and heated at 160° C. for 10 minutes in a microwave reactor. The reaction was cooled to rt, diluted with EtOAc:hexanes (2:1, 20 mL) and washed with water (2×20 mL) and brine (20 mL). The organic phase was dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by column chromatography (silica gel) using 0 to 10% EtOAc/hexanes to afford (E)-ethyl 4-styrylbenzoate (771 mg, 85%) as a pale yellow solid; 1H-nmr (400 MHz, CDCl3) δ 8.05 (d, J=8.0 Hz, 2H), 7.61 (d, J=8.0 Hz, 2H), 7.56 (dd, J=8.0, 2.0 Hz, 2H), 7.41-7.37 (m, 3H), 6.95 (d, 1H), 6.89 (d, 1H), 4.41 (q, J=7.0 Hz, 2H), 1.44 (t, J=6.8 Hz, 3H); LCMS (214 nM) 3.58 min (>98%); MS (ESI) m/z=253.1.

후처리

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was cooled to rt
  3. washwashed with water (2×20 mL) and brine (20 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by column chromatography (silica gel)

출처 및 근거

ORD 기록
ord-1d808382e8eb4434bdad84625400cc12
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853392B2

반응 노트

불러오는 중…