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Methanol → (E)-3-[4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]phenyl]-2-propen-1-ol

HRID 1740907
Notes
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Reaction equation

HRID 1740907 reaction equation
C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[CH3:18][C:19]1[O:23][C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=2)=[N:21][C:20]=1[CH2:31][CH2:32][O:33][C:34]1[CH:46]=[CH:45][C:37](/[CH:38]=[CH:39]/[C:40](OCC)=[O:41])=[CH:36][CH:35]=1.CO>ClCCl.O>[CH3:18][C:19]1[O:23][C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=2)=[N:21][C:20]=1[CH2:31][CH2:32][O:33][C:34]1[CH:35]=[CH:36][C:37](/[CH:38]=[CH:39]/[CH2:40][OH:41])=[CH:45][CH:46]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 86751224ethyl (E)-4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamate

Product 1

HCID 18546146(E)-3-[4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]phenyl]-2-propen-1-olYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A toluene solution of diisobutylaluminum hydride (1.5M, 9.3 ml) was added dropwise at 0° C. to a suspension of ethyl (E)-4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]cinnamate (2.48 g) in dichloromethane (50 ml). The mixture was stirred for 2 hours at room temperature, to which were then added, under ice-cooling, methanol (3 ml) and, then, water (30 ml). The mixture was subjected to filtration through a celite layer. The organic layer was washed with water, dried (MgSO4) and, then, concentrated. The concentrate was purified by means of a column chromatography. From the fractions eluted with ethyl acetate-hexane (1:1) was obtained (E)-3-[4-[2-[5-methyl-2-(3-methylphenyl)-4-oxazolyl]ethoxy]phenyl]-2-propen-1-ol (1.44 g, 65%). Recrystallization from dichloromethane-isopropyl ether gave colorless prisms, m.p.116-117° C.

Workup

  1. additionwere then added, under ice-
  2. temperaturecooling
  3. filtrationThe mixture was subjected to filtration through a celite layer
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe concentrate was purified by means of a column chromatography
  8. washFrom the fractions eluted with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-83e177466cae4cc687fc62a643804226
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05972970

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes