Water → [5-Methyl-2-(2-phenylethenyl)-1,3-oxazol-4-yl]methanol

HRID 746015Notes

Reaction equation

HRID 746015 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][C:3]=1[C:15](OCC)=[O:16].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1.C(OCC)C>[OH:16][CH2:15][C:3]1[N:4]=[C:5]([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54276390Ethyl 5-methyl-2-(2-phenylethenyl)-1,3-oxazole-4-carboxylate

Product 1

HCID 54521586[5-Methyl-2-(2-phenylethenyl)-1,3-oxazol-4-yl]methanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-methyl-2-styryl-4-oxazolecarboxylate (2.14 g) was dissolved in a mixture of dry tetrahydrofuran (10 ml) and dry ethyl ether (15 ml) and the solution was added dropwise to a suspension of lithiumaluminum hydride (0.34 g) in dry ethyl ether (20 ml) with ice-cooling and stirring. The mixture was further stirred under ice-cooling for an hour and water (2 ml) was added portionwise for decomposition. The precipitate was filtered off and the filtrate was concentrated to give 4-hydroxymethyl-5-methyl-2-styryloxazole as crystals; yield 1.28 g (71.5%). Recrystallization from acetone gave colorless prisms melting at 106°-107° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was further stirred under ice-
  3. temperaturecooling for an hour
  4. filtrationThe precipitate was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cae4c745ba4649f0a8a58f0ccd1474e6
Source dataset
uspto-grants-1986_07
Patent number
US04602027

Reaction notes

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