Water → trans-3-Octen-1-ol

HRID 1470687

반응식

HRID 1470687 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7](O)(=[O:15])[CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH3:14].O.[OH-].[Na+]>C1COCC1>[CH2:7]([OH:15])[CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH3:14]

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 5282716(E)-Oct-3-enoic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 5364475trans-3-Octen-1-ol수율 76.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

LiAlH4 (13.5 mL, 13.5 mmol, 1 M/THF) was added to an ice cold solution of (E)-oct-3-enoic acid (7-1, 1.86 g, 13.1 mmol) in THF (48 mL). The reaction was allowed to warm to room temperature and after 2 h, was cooled in an ice bath and 50 mL H2O was added slowly. NaOH (3 M, 50 mL) and H2O (50 mL) were added and the resulting mixture was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (100 mL) and was then dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit) gave the title compound (1.283 g, 76%).

후처리

  1. temperaturewas cooled in an ice bath
  2. extractionthe resulting mixture was extracted with dichloromethane (3×100 mL)
  3. washThe combined organic layer was washed with brine (100 mL)
  4. dry with materialwas then dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (Isco Combiflash unit)

출처 및 근거

ORD 기록
ord-85b4bd52aa6848f5bf8fa8c7e9ecf861
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006464B2

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