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

HRID 1892645ノート

反応式

HRID 1892645 の反応式
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Cl-].[Li+].C([Mg]Cl)(C)C.[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

参加物

5

反応物 3

HCID 69273Methyl 4-iodobenzoateHCID 103078492-CyclopropylacetaldehydeHCID 178461733HCID 178461733、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

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), 0.49-0.25 (m, 2H), 0.07-−0.12 (m, 2H).

後処理

  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

出典と根拠

ORDレコード
ord-eeadefaffe564da993e558109f3c4bcf
出典データセット
uspto-grants-2013_08
特許番号
US08507533B2

反応ノート

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