Hydrochloric Acid → (Z)-3-(4-methoxyphenyl)-3-(3-pyridinyl)-2-propenal

HRID 2232796노트

반응식

HRID 2232796 반응식
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=O)=[CH:5][CH:4]=1.C(NC(C)C)(C)C.C([Li])CCC.Cl.[CH2:30]([O:32]P(Cl)(=O)OCC)[CH3:31]>CCCCCC.C(N=CC)(C)(C)C.O1CCCC1>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6](/[C:7](/[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:31]/[CH:30]=[O:32])=[CH:5][CH:4]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 13139Diethyl chlorophosphateHCID 32108(4-Methoxyphenyl)-3-pyridinylmethanoneHCID 178418339Butyllithium

생성물 1

HCID 14994117(Z)-3-(4-methoxyphenyl)-3-(3-pyridinyl)-2-propenal

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 138901N-Ethylidene-2-methylpropan-2-amine용매

실험 절차

The compounds were prepared according to the procedure described in Example 84 except that the reaction was worked up after 17 hours. The following reagents were used: 3-(4-methoxybenzoyl)pyridine (22 g), diisopropylamine (32.2 mL), 1.55M n-butyl lithium in hexane (148 mL), acetaldehyde N-tert-butylimine (14.75 mL), diethylchlorophosphonate (16.6 mL) and tetrahydrofuran (200 mL). The work up, varied only in that the hydrolysis step was done by treating the intermediate imine with 2N HCl (300 ml) for 9 hours at 70° C. furnished, after basification and extraction, 24 g of crude material made up of a mixture of (E)-3-(4-methoxyphenyl)-3-(3-pyridinyl)-2-propenal and (Z)-3-(4-methoxyphenyl)-3-(3-pyridinyl)-2-propenal. purification of the crude by HPLC (ether; 3 recycles) provided 5.45 g of the less polar aldehyde, (E)-3-(4-methoxyphenyl)-3-(3-pyridinyl)-2-propenal along with 11 g of the isomer (Z)-3-(4-methoxyphenyl)-3-(3-pyridinyl)-2-propenal as oils.

후처리

  1. customThe compounds were prepared
  2. customThe work up, varied only in that the hydrolysis step
  3. customfurnished
  4. extractionafter basification and extraction, 24 g of crude material
  5. additionmade up of a mixture of (E)-3-(4-methoxyphenyl)-3-(3-pyridinyl)-2-propenal and (Z)-3-(4-methoxyphenyl)-3-(3-pyridinyl)-2-propenal
  6. custompurification of the crude by HPLC (ether; 3 recycles)

출처 및 근거

ORD 기록
ord-ce9bac8aae6b421d82e17ea7cfdd83d7
출처 데이터셋
uspto-grants-1988_11
특허 번호
US04788206

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