Hydrochloric Acid → (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal

HRID 48545

반응식

HRID 48545 반응식
[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH2:4][OH:5].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[N+](C1C=C(C=CC=1)C=O)([O-])=O.Cl>C1CCCCC1.CCCCCC>[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH:4]=[O:5]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 74493-NitrobenzaldehydeHCID 11143Aluminum isopropoxideHCID 445070Farnesol

생성물 1

HCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal수율 96%

시약·촉매·용매 2

HCID 8058Hexane용매HCID 8078Cyclohexane용매

실험 절차

(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol (445 mg, 2.0 mmol) was dissolved in cyclohexane (1 mL), added with aluminum isopropoxide (40 mg, 0.1 eq, 0.2 mmol) and 3-nitrobenzaldehyde (393 mg, 1.3 eq, 2.6 mmol) and stirred at room temperature for 2 hours. The reaction mixture was added with hexane, then made acidic with addition of 1 N hydrochloric acid and extracted twice with ethyl acetate. Subsequently, the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain 427 mg (yield: 96%, E:Z=99:1) of the title compound as yellow oil.

후처리

  1. extractionextracted twice with ethyl acetate
  2. washSubsequently, the organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

출처 및 근거

ORD 기록
ord-e95a46d4355c47f6afb7014336a8dda3
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703527B2

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