Ethyl Acetate → HCID 67176075, compound

HRID 1027488Notes

Reaction equation

HRID 1027488 reaction equation
[C:1]1([C:7]([Mg]Br)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS([C:15]1[N:16]=[C:17]([O:31][CH2:32][CH2:33][CH3:34])[C:18]2[N:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=3)[O:21][C:19]=2[N:20]=1)(=O)=O.[Cl-].[Li+].C(OCC)(=O)C>O1CCCC1>[C:1]1([C:7]([C:15]2[N:16]=[C:17]([O:31][CH2:32][CH2:33][CH3:34])[C:18]3[N:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=4)[O:21][C:19]=3[N:20]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 67175734HCID 67175734, compoundHCID 178462449HCID 178462449, compound

Product 1

HCID 67176075HCID 67176075, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

298 mg of 1-phenyl-vinylmagnesium bromide were added to a solution of 500 mg of 5-methanesulfonyl-7-propoxy-2-(3-methyl-phenyl)-oxazolo[5,4-d]pyrimidine (example 5, step (f)) and 61 mg of lithium chloride in 20 ml of tetrahydrofuran. The reaction mixture was stirred for 1 h. Then 100 ml of ethyl acetate were added. The solution was extracted with 1 N hydrochloric acid, dried over sodium sulfate, filtered and evaporated in vacuo to give the crude title compound.

Workup

  1. extractionThe solution was extracted with 1 N hydrochloric acid
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-bda3d67a92c247908be9523e28d477f7
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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