Methanol → HCID 19965653, compound

HRID 977255Notes

Reaction equation

HRID 977255 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:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)=[N:21][C:20]=1[CH:34]=[CH:35][C:36]1[CH:48]=[CH:47][C:39](/[CH:40]=[CH:41]/[C:42](OCC)=[O:43])=[CH:38][CH:37]=1.CO>ClCCl.O>[CH3:18][C:19]1[O:23][C:22]([C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=2)=[N:21][C:20]=1/[CH:34]=[CH:35]/[C:36]1[CH:37]=[CH:38][C:39](/[CH:40]=[CH:41]/[CH2:42][OH:43])=[CH:47][CH:48]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 86750603HCID 86750603, compound

Product 1

HCID 19965653HCID 19965653, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A toluene solution of diisobutylaluminum hydride (1.5 M, 17 ml) was added drop by drop to a suspension of ethyl (E)-4-[2-[5-methyl-2-(2-naphthyl)4-oxazolyl]vinyl]cinnamate (4.20 g) in dichloromethane (100 ml) at 0° C. After the mixture was stirred at room temperature for 4 hours, methanol (2 ml) and then water (6 ml) were added at 0° C. After the insoluble substances were filtered off, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to yield a crystal of (E,E)-3-[4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]vinyl]phenyl]-2-propenol from the fraction eluted with ethyl acetate-chloroform (5:95, v/v), which was then recrystallized from chloroform-ethanol to yield light yellow prisms (3.04 g, 81%) having a melting point of 184°-185° C.

Workup

  1. filtrationAfter the insoluble substances were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d3d3aae4351a43a5a4955dcf4605dc30
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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