Hydrochloric Acid → HCID 10893028, compound

HRID 233280Notes

Reaction equation

HRID 233280 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1[O:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][C:13]=1[CH2:23][CH2:24][O:25][C:26]1[CH:38]=[CH:37][C:29]([CH:30]=[CH:31][C:32](OCC)=[O:33])=[CH:28][CH:27]=1.Cl>C1(C)C=CC=CC=1>[CH3:11][C:12]1[O:16][C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:14][C:13]=1[CH2:23][CH2:24][O:25][C:26]1[CH:38]=[CH:37][C:29](/[CH:30]=[CH:31]/[CH2:32][OH:33])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 54499671HCID 54499671, compound

Product 1

HCID 10893028HCID 10893028, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A toluene solution of diisobutylaluminum hydride (1.5M, 67 ml) was added dropwise at 0° C. to a suspension of ethyl 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]cinnamate (15.0 g) in toluene (200 ml). The mixture was stirred for 2 hours at room temperature, to which was added 2N HCl (200 ml) under ice-cooling. The organic layer was washed with water, dried (MgSO4) and concentrated to give (E)-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]-2-propen-1-ol (12,0 g, 90%), which was recrystallized from ethyl acetate to give colorless prisms, m.p.127°-128° C.

Workup

  1. temperaturecooling
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-238b6d3b20784f369412f2ec14946058
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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