Ethyl Acetate → HCID 54564593, compound

HRID 581900Notes

Reaction equation

HRID 581900 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17](OC(C)C)=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.C(OCC)(=O)C>C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH2:17][OH:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 53709126HCID 53709126, compound

Product 1

HCID 54564593HCID 54564593, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred suspension of 26 from Example 5 (18 g, 50.18 mmol) in 300 ml dry diethyl ether is kept under a stream of nitrogen at room temperature. LiAIH4 (1.9 g, 50 mmol) is added in portions and the mixture is stirred over night. The mixture is poured into a mixture of ice-water and ethyl acetate. The resulting emulgation is filtered through celite and the phases are separated. The aqueous phase is extracted once with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographied on silica gel using successively ethyl acetate and a mixture of ethyl acetate and methanol (9:1) as eluents. Yield of 27: 7.69 g (51%). Mp 107-109° C.

Workup

  1. customis kept under a stream of nitrogen at room temperature
  2. additionLiAIH4 (1.9 g, 50 mmol) is added in portions
  3. filtrationThe resulting emulgation is filtered through celite
  4. customthe phases are separated
  5. extractionThe aqueous phase is extracted once with ethyl acetate
  6. washThe combined organic phases are washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additiona mixture of ethyl acetate and methanol (9:1) as eluents

Sources & evidence

ORD record
ord-3e7e2a4f32d242c589abb2fce691ad3e
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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