Dichloromethane → Methyl 7-[3-ethoxy-4-(2-propoxyethoxy)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

HRID 1169472노트

반응식

HRID 1169472 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1.[CH2:19]([O:21][C:22]1[CH:23]=[C:24](OB(O)O)[CH:25]=[CH:26][C:27]=1[O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH3:34])[CH3:20].ClCCl>C(N(CC)CC)C>[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH3:34])[O:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1)[CH3:20]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 22989977Methyl 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylateHCID 229900413-Ethoxy-4-(2-propoxyethoxy)phenylboric acid

생성물 1

HCID 22990043Methyl 7-[3-ethoxy-4-(2-propoxyethoxy)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate수율 61.5%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

To a mixture of methyl 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.40 g), 3-ethoxy-4-(2-propoxyethoxy)phenylboric acid (0.80 g), cupric acetate (0.27 g), MS4A (0.8 g) and dichloromethane (15 ml) was added at room temperature triethylamine (1.04 ml), and the resulting mixture was stirred for 16 hours. The reaction mixture was filtered to remove an insoluble material and the filtrate was concentrated under reduced pressure. The residue was subjected to separation and purification using column chromatography (ethyl acetate:hexane 1:2→2:3) to obtain methyl 7-[3-ethoxy-4-(2-propoxyethoxy)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.45 g) as a light yellow, oily substance. 1H-NMR (200 MHz, CDCl3) δ0.95 (3H, t, J=7.4 Hz), 1.44 (3H, t, J=7.0 Hz), 1.56-1.70 (2H, m), 3.04-3.11 (2H, m), 3.53 (2H, t, J=6.8 Hz), 3.58-3.65 (2H, m), 3.80-3.85 (5H, m), 4.03 (2H, q, j=7.0 Hz), 4.17-4.22 (2H, m), 6.56-6.63 (2H, m), 6.94-7.04 (3H, m), 7.70 (1H, s), 8.08 (1H, d, J=8.4 Hz).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customto remove an insoluble material
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was subjected to separation and purification

출처 및 근거

ORD 기록
ord-bdd9d8d8cb454382b92bbc3c97661eeb
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627651B1

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