Water → HCID 70108314, compound

HRID 977250Notes

Reaction equation

HRID 977250 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1/[CH:17]=[CH:18]/[C:19]1[CH:28]=[CH:27][C:22]([C:23](OC)=[O:24])=[CH:21][CH:20]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1/[CH:17]=[CH:18]/[C:19]1[CH:20]=[CH:21][C:22]([CH2:23][OH:24])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86750601HCID 86750601, compound

Product 1

HCID 70108314HCID 70108314, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl (E)-4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]vinyl]benzoate (9.30 g) was suspended in THF (250 ml), and lithium aluminum hydride (955 mg) was added little by little at 0° C. After mixture stirring at room temperature for 1 hour, water (5 ml) was added; the insoluble substances were filtered off. The filtrate was concentrated under reduced pressure; the resulting crystal was recrystallized from dichloromethane-methanol to yield (E)-4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]vinyl]benzyl alcohol (8.00 g, 93%) as colorless prisms having a melting point of 173°-174° C.

Workup

  1. filtrationthe insoluble substances were filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resulting crystal was recrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-83ef59a44b4b4a78977b2798a524475f
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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