Triethyl phosphite → (E)-Ethyl 3-(dimethylamino)-5-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoate

HRID 2368875노트

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HRID 2368875 반응식
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([N:14]([CH3:16])[CH3:15])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(OP(OCC)OCC)C.C[O-].[Na+].[CH3:30][O:31][CH2:32][O:33][C:34]1[C:41]([CH3:42])=[CH:40][C:37]([CH:38]=O)=[CH:36][C:35]=1[CH3:43]>CCOC(C)=O.CCO.CN(C=O)C>[CH3:15][N:14]([CH3:16])[C:12]1[CH:11]=[C:5]([CH:4]=[C:3](/[CH:2]=[CH:38]/[C:37]2[CH:40]=[C:41]([CH3:42])[C:34]([O:33][CH2:32][O:31][CH3:30])=[C:35]([CH3:43])[CH:36]=2)[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

8

반응물 4

HCID 31215Triethyl phosphiteHCID 10942334Sodium MethoxideHCID 199197474-(Methoxymethoxy)-3,5-dimethylbenzaldehydeHCID 68335175Ethyl 3-(chloromethyl)-5-(dimethylamino)benzoate

생성물 1

HCID 68335176(E)-Ethyl 3-(dimethylamino)-5-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoate수율 67.1%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

Compound 3 (1.224 g, 4.277 mmol) and triethylphosphite (1.512 mL, 8.555 mmol) were heated to 150° C. for 3 hours. The reaction mixture was cooled to 0° C. and then 6 mL of DMF and 6 mL of EtOH were added. NaOMe (486 mg, 8.554 mmol) and 4-(methoxymethoxy)-3,5-dimethylbenzaldehyde (0.831 g, 4.277 mmol) were added to the solution. After 18 hours, the mixture was diluted with EtOAc and the solution was washed with brine. After drying on Na2SO4, the organic layer was filtered and concentrated under reduced pressure. The residue was subjected to chromatography over silica gel (Hexanes/EtOAc=9/1) to give Compound 4 (1.10 g, 67%). 1H-NMR (500 MHz, CDCl3) δ 7.56 (s, 1H), 7.30 (m, 1H), 7.20 (s, 2H), 7.06 (d, J=16.3 Hz, 1H), 6.99 (d, J=16.3 Hz, 1H), 6.97 (s, 1H), 4.96 (s, 2H), 4.39 (q, J=7.1 Hz, 2H), 3.62 (s, 3H), 3.03 (s, 6H), 2.32 (s, 6H), 1.42 (t, J=7.1 Hz, 3H); 13C-NMR (125 MHz, CDCl3) δ 167.23, 154.65, 150.72, 138.36, 133.12, 131.48, 131.24, 128.70, 127.78, 127.07, 115.70, 114.53, 112.47, 99.11, 60.92, 57.39, 40.65, 16.99, 14.40; ESI-MS: m/z (MH+): 384.2169 (calc'd), 384.2173 (found).

후처리

  1. washthe solution was washed with brine
  2. customAfter drying on Na2SO4
  3. filtrationthe organic layer was filtered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ef0868bad66a4a21addde9927a991964
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703815B2

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