Methyl 4-iodobenzoate → Methyl 4-(2-cyclopropyl-1-hydroxyethyl)benzoate

HRID 537432노트

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HRID 537432 반응식
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[Cl-].[Li+].[CH:19]1([CH2:22][CH:23]=[O:24])[CH2:21][CH2:20]1>O1CCCC1>[CH:19]1([CH2:22][CH:23]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=2)[OH:24])[CH2:21][CH2:20]1

참가 물질

5

반응물 3

HCID 69273Methyl 4-iodobenzoateHCID 103078492-CyclopropylacetaldehydeHCID 178461733HCID 178461733, 화합물

생성물 1

HCID 68178576Methyl 4-(2-cyclopropyl-1-hydroxyethyl)benzoate수율 45.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-40 °C

실험 절차

To a −40° C. solution of methyl 4-iodobenzoate (0.39 g, 1.5 mmol) in tetrahydrofuran (7.5 mL) was added isopropylmagnesium chloride-lithium chloride (1.5 mL, 1.3 M in THF, 1.95 mmol) dropwise. After stirring for 30 minutes at −40° C., 2-cyclopropylacetaldehyde (190 mg, 2.26 mmol) was added dropwise. The resulting mixture was then stirred at room temperature for 1 hour. The reaction mixture was quenched with saturated ammonium chloride and partitioned between water and ethyl acetate. The layers were separated and the aqueous was extracted again with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave (+/−)-methyl 4-(2-cyclopropyl-1-hydroxyethyl)benzoate (150 mg, 45%). 1HNMR (400 MHz, CDCl3, δ): 7.89 (d, 2H), 7.32 (d, 2H), 4.75-4.72 (m, 1H), 3.79 (s, 3H), 1.60-1.51 (m, 2H), 0.60-0.51 (m, 1H), 0.49-025 (m, 2H), 0.07-0.12 (m, 2H).

후처리

  1. stirringThe resulting mixture was then stirred at room temperature for 1 hour
  2. customThe reaction mixture was quenched with saturated ammonium chloride
  3. custompartitioned between water and ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous was extracted again with ethyl acetate
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography

출처 및 근거

ORD 기록
ord-61b1434b877a4fc9987f05235c9155e2
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859591B2

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