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Propanal → 4-Nitro-3-hexanol

HRID 909991
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HRID 909991 반응식
[N+:1](CCC)([O-:3])=[O:2].[CH2:7]1[CH2:17][CH2:16]N2[C:10](=NCCC2)[CH2:9][CH2:8]1.C(=[O:21])CC>C(OCC)(=O)C>[OH:21][CH:7]([CH2:17][CH3:16])[CH:8]([N+:1]([O-:3])=[O:2])[CH2:9][CH3:10]
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참가 물질

5

반응물 3

HCID 527PropanalHCID 79031-NitropropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

생성물 1

HCID 2206384-Nitro-3-hexanol수율 837.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A reaction vessel was replaced with nitrogen, and 1-nitropropane (8.93 ml, 100 mmol) and dry-THF (50 ml) were added. After DBU (1,8-diazabicyclo[5.4.0]-7-undecene) (1.5 ml, 10 mmol) had been added, propionaldehyde (4.68 ml, 100 mmol) was added while the vessel was cooled in an ice bath. After the mixture had been stirred at room temperature for 10 hours, ethyl acetate (100 ml) was added, and the whole was washed with dilute hydrochloric acid, water, and a saturated salt solution. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to yield 4-hydroxy-3-nitrohexane (12.33 g, 84% yield).

후처리

  1. dry with materialdry-THF (50 ml)
  2. additionwere added
  3. temperaturewas cooled in an ice bath
  4. washthe whole was washed with dilute hydrochloric acid, water
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d86b3209a13340678209556d5317e7fd
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08021915B2

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