Hydrochloric Acid → HCID 10337891, compound

HRID 322240Notes

Reaction equation

HRID 322240 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1(/[CH:13]=[CH:14]/[C:15]2[O:16][CH:17]=[C:18]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][C:31](OCC)=[O:32])=[CH:24][CH:23]=3)[N:19]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O1CCCC1.Cl>C(OCC)C.O>[C:7]1(/[CH:13]=[CH:14]/[C:15]2[O:16][CH:17]=[C:18]([CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][OH:32])=[CH:26][CH:27]=3)[N:19]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 22009786HCID 22009786, compound

Product 1

HCID 10337891HCID 10337891, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of lithium aluminum hydride (350 mg) in diethyl ether (10 ml) was added dropwise, at 0° C., a solution of ethyl 4-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]butyrate (3.00 g) in diethyl ether (10 ml)—tetrahydrofuran (10 ml). The mixture was stirred at 0° C. for one hour and at room temperature for further one hour, followed by addition of water. The mixture was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:1,v/v), 4-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]butanol (2.00 g, 74%) was obtained. Recrystallization from ethyl acetate-hexane afforded colorless needles, mp 90-91° C.

Workup

  1. additionwas added dropwise, at 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washFrom the fraction eluted with ethyl acetate-hexane (1:1,v/v)

Sources & evidence

ORD record
ord-fb01c660f4aa4634aea045a458ac458f
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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