Hydrochloric Acid → HCID 21840272, compound

HRID 1584331Notes

Reaction equation

HRID 1584331 reaction equation
C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:30]=[CH:31][C:32]=1[O:33][CH2:34][C:35]1[N:36]=[C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:38][CH:39]=1)[CH:23]=[CH:24][C:25](OCC)=[O:26].Cl>O1CCCC1.CO>[CH3:18][O:19][C:20]1[CH:21]=[C:22](/[CH:23]=[CH:24]/[CH2:25][OH:26])[CH:30]=[CH:31][C:32]=1[O:33][CH2:34][C:35]1[N:36]=[C:37]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[O:38][CH:39]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 53705954HCID 53705954, compound

Product 1

HCID 21840272HCID 21840272, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A toluene solution of diisobutylaluminum hydride (1.5M, 72.2 ml) was added dropwise, at 0° C., to a solution of ethyl 3-methoxy-4-(2-phenyl-4-oxazolylmethoxy)cinnamate (16.4 g) in tetrahydrofuran (THF) (240 ml). The mixture was stirred for 2 hours at room temperature, to which was added, under ice-cooling, methanol (7 ml). The reaction mixture was poured into 2N HCl (600 ml), which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated to yield (E)-3-[3-methoxy-4-(2-phenyl-4-oxazolylmethoxy)phenyl]-2-propen-1-ol (14.4 g, 98%), which was recrystallized from ethyl acetate-hexane to give colorless needles, m.p.113-114° C.

Workup

  1. additionwas added, under ice-
  2. temperaturecooling
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-81eb89bdabd945fbaeeeafecec5a4285
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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