Triethyl phosphonoacetate → ethyl-E-4-(3-methoxyphenyl)-4-methylpent-2-enoate

HRID 1444534노트

반응식

HRID 1444534 반응식
[CH3:1][CH2:2][O:3][C:4]([CH2:6]P(OCC)(OCC)=O)=[O:5].[Li+].CC([N-]C(C)C)C.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:31]([CH3:35])([CH3:34])[CH:32]=O)[CH:28]=[CH:29][CH:30]=1.[Cl-].[NH4+]>C1COCC1.CCCCCCC.C(C1C=CC=CC=1)C.O1CCCC1>[CH2:2]([O:3][C:4](=[O:5])/[CH:6]=[CH:35]/[C:31]([C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([O:24][CH3:23])[CH:26]=1)([CH3:32])[CH3:34])[CH3:1]

참가 물질

7

반응물 4

HCID 13345Triethyl phosphonoacetateHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 132969932-(3-Methoxyphenyl)-2-methylpropanal

생성물 1

HCID 86599931ethyl-E-4-(3-methoxyphenyl)-4-methylpent-2-enoate수율 95.8%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 22742125Tetrahydrofuran heptane ethylbenzol용매

실험 절차

33.6 g (114.3 mmol) of phosphonoacetic acid triethyl ester is introduced into 148 ml of tetrahydrofuran. At 0° C., 79.7 ml of a 2 M solution of LDA in THF/heptane/ethylbenzene is added in drops (1½ hours). After one hour of stirring, 24.3 g (136.34 mmol) of 2-(3-methoxyphenyl)-2-methylpropanal, dissolved in 130 ml of tetrahydrofuran, is added in drops at 0° C. After five days of stirring at room temperature, the reaction mixture is poured into 250 ml of dilute ammonium chloride solution and extracted twice with 400 ml each of diethyl ether. The combined organic extracts are treated as usual, and the residue that is obtained is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 27.2 g (80.4%) of the desired compound is isolated.

후처리

  1. additionis added in drops at 0° C
  2. stirringAfter five days of stirring at room temperature
  3. extractionextracted twice with 400 ml each of diethyl ether
  4. additionThe combined organic extracts are treated as usual, and the residue that
  5. customis obtained
  6. customis chromatographed on silica gel (mobile solvent ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-df5b3e0ccc6e4faa86fa856cacba9f74
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662821B2

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