Hexanal → 2-(1-Hydroxyhexyl)-3-(1-octen-1-yl)-4-isopropyl cyclohexanone

HRID 1654258

反応式

HRID 1654258 の反応式
[CH:1]([CH:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH:6]=[CH:5]1)([CH3:3])[CH3:2].[CH:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C1COCC1.[Cu]>[OH:17][CH:11]([CH:6]1[CH:5]([CH:2]=[CH:1][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:4]([CH:1]([CH3:3])[CH3:2])[CH2:9][CH2:8][C:7]1=[O:10])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

参加物

5

反応物 2

HCID 6184HexanalHCID 927804-Isopropyl-2-cyclohexenone

生成物 1

HCID 539565772-(1-Hydroxyhexyl)-3-(1-octen-1-yl)-4-isopropyl cyclohexanone収率 82%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Following the procedure of Example 1, a mixed solution was formed of the cuprate and Me3ZnLi (0.52 mmol) comprising 10 mol-% of copper per mole of enone. The solution was treated with 4-isopropyl-2-cyclohexenone (77 μL, 0.5 mmol) as a neat liquid over 70 minutes and then stirred for an additional 2 hours. Hexanal (0.25 mL, 2.0 mmol), in 1.0 mL THF at -78° C., was then added. After 5 minutes the mixture was quenched with 5 mL of 10% NH4OH in saturated NH4Cl. The product was extracted with 3×20 mL of ether and dried over Na2SO4. The solution was then filtered through flitted filter paper and the solvent removed in vacuo. The resulting residue was submitted to flash chromatography on silica gel (Petroleum Ether/Ethyl Acetate, 30/1) to give an 82% yield of 2-(1-hydroxyhexyl)-3-(1-octen-1-yl)-4-isopropyl cyclohexanone as a colorless oil which gave satisfactory IR, NMR, MS, and HRMS data.

後処理

  1. customAfter 5 minutes the mixture was quenched with 5 mL of 10% NH4OH in saturated NH4Cl
  2. extractionThe product was extracted with 3×20 mL of ether
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution was then filtered
  5. filtrationthrough flitted filter paper
  6. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-e4c50389068a4113a749e10673ab8ad3
出典データセット
uspto-grants-1995_04
特許番号
US05405981

関連ノート

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