HCID 59745010, compound → HCID 59744997, compound

HRID 2402429Notes

Reaction equation

HRID 2402429 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:9]=[CH:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=1>C1COCC1>[OH:9][CH:10]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 59745010HCID 59745010, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 59744997HCID 59744997, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A 1.0 M solution of PhMgBr (1 equiv, 0.45 mmol) was added dropwise to a solution of methyl 2-(3-(4-oxobutyl)phenyl)acetate (1 equiv, 100 mg, 0.45 mmol) in THF (2 mL) at 0° C. The reaction was then allowed to warm to 23° C. over 1 h. The reaction was quenched by the addition on sat. aq. NH4Cl (10 mL). The aqueous phase was separated and extracted with EtOAc (2×5 mL). The organic layers were then combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluting with 0-50% EtOAc in hexanes to afford methyl 2-(3-(4-hydroxy-4-phenylbutyl)phenyl)acetate in 78 mg (58%) as a clear translucent oil. LRMS: 298.4 (calc) 321.2 (found)(MH)+.

Workup

  1. customThe reaction was quenched by the addition on sat. aq. NH4Cl (10 mL)
  2. customThe aqueous phase was separated
  3. extractionextracted with EtOAc (2×5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel column chromatography
  8. washeluting with 0-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-c8c8b99d159f41e98d3c97ecd0b4d4a0
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

Loading…