Benzyl Bromide → HCID 86590041, compound

HRID 857523Notes

Reaction equation

HRID 857523 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]1[C:8](=[O:18])[O:9][C:10]2[C:15]([C:16]=1[OH:17])=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:2].[Li+].CC([N-]C(C)C)C.[CH:28]1[CH:33]=[CH:32][C:31]([CH2:34]Br)=[CH:30][CH:29]=1>C1COCC1>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([CH2:34][C:31]1[CH:32]=[CH:33][CH:28]=[CH:29][CH:30]=1)[CH2:6][C:7]1[C:8](=[O:18])[O:9][C:10]2[C:15]([C:16]=1[OH:17])=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 2724682Lithium diisopropylamideHCID 86590040HCID 86590040, compound

Product 1

HCID 86590041HCID 86590041, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-propionic acid ethyl ester in THF at −78° C. was added LDA (1.5M, 3.05 mL) dropwise. A yellow precipitate was formed during the addition. The reaction was stirred at −78° C. for 15 min and allowed to warmed to 0° C. and stirred for 30 min, after which BnBr (0.24 mL in THF) was added dropwise. The reaction was warmed to room temperature, stirred for 12 hours, cooled to 0° C. and quenched with saturated ammonium chloride and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and conc. in vacuo to a crude colorless oil, which was purified by column chromatography to provide 2-Benzyl-3-(4-hydroxy-2-oxo-2H-chromen-3-yl)-propionic acid ethyl ester as a colorless oil (250 mg). MS: 351[M−H].

Workup

  1. customA yellow precipitate was formed during the addition
  2. temperatureallowed to warmed to 0° C.
  3. stirringstirred for 30 min
  4. temperatureThe reaction was warmed to room temperature
  5. stirringstirred for 12 hours
  6. temperaturecooled to 0° C.
  7. customquenched with saturated ammonium chloride
  8. extractionextracted with EtOAc
  9. washThe organic layer was washed with brine
  10. dry with materialdried over MgSO4 and conc. in vacuo to a crude colorless oil, which
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-920a2cca56264e3f84d6baafdcc52411
Source dataset
uspto-grants-2006_12
Patent number
US07145020B2

Reaction notes

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