Ethyl bromoacetate → HCID 15027645, compound

HRID 1090647Notes

Reaction equation

HRID 1090647 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OCC)=O.[CH:52]([C:54]1[C:59](=[O:60])[N:58]([CH2:61][CH2:62][CH3:63])[C:57](=[O:64])[N:56]2[CH2:65][CH2:66][S:67][C:55]=12)=O>C(Cl)Cl>[O:64]=[C:57]1[N:56]2[CH2:65][CH2:66][S:67][C:55]2=[C:54](/[CH:52]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:59](=[O:60])[N:58]1[CH2:61][CH2:62][CH3:63]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11776TriphenylphosphineHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 15027643HCID 15027643, compound

Product 1

HCID 15027645HCID 15027645, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the Wittig reagent prepared from triphenylphosphine (5.3 g) and ethyl bromoacetate (3.4 g), (carboethoxymethylene)triphenylphosphorane (6 g) and 8-formyl-6-propyl-2,3-dihydro-5H-thiazolo[3,2-c]pyrimidine-5,7(6H)-dione (3.76 g) in methylene chloride (15 ml) was refluxed in for 7 hours. The reaction solution was concentrated to dryness. The resulting residue was purified by column chromatography on silica gel. The resulting crude crystals were recrystallized from methylene chloride -isopropyl ether to give colorless needles (3.82 g, 79%).

Workup

  1. temperaturewas refluxed in for 7 hours
  2. concentrationThe reaction solution was concentrated to dryness
  3. customThe resulting residue was purified by column chromatography on silica gel
  4. customThe resulting crude crystals were recrystallized from methylene chloride -isopropyl ether

Sources & evidence

ORD record
ord-a150859f41e840298c3816e9ab63e27a
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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