HCID 87212268, compound → HCID 25030274, compound

HRID 2280582Notes

Reaction equation

HRID 2280582 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=1.[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[OH:10])[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=1

Participants

4

Reactant 2

HCID 87212268HCID 87212268, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 25030274HCID 25030274, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

The aldehyde 5 were dissolved in dry THF and cooled to −20° C. Phenylmagnesium bromide (1.2 eq, 1.651 mM) was then added to the reaction and the reaction was stirred for an additional 2 hrs. After the completion of the reaction as determined by TLC, the reaction mixture was quenched with 0.1 N HCl, followed by washes with saturated sodium bicarbonate solution and brine. The organic layer was then evaporated and the product was purified by flash chromatography using 20% EtOAc/Hexanes as the solvent system to obtain a white solid. Yield=78.0% (Rf=0.48; 20% EtOAc/Hexanes) 1H NMR, 500 MHz Varian, CDCl3, δ 10.01 (s, 1H), 7.53 (d, J=15.00 Hz, 1H), 7.51 (d, J=15.00 Hz, 1H), 7.49 (d, J=10.00 Hz, 1H), 7.34 (s, 3H), 7.21 (d, J=7.0, 1H), 3.89 (s, 3H), 2.41 s, 3H), MS: m/z (ESI, pos.)=327.8 ([M+23])

Workup

  1. customAfter the completion of the reaction
  2. customthe reaction mixture was quenched with 0.1 N HCl
  3. customThe organic layer was then evaporated
  4. customthe product was purified by flash chromatography
  5. customto obtain a white solid

Sources & evidence

ORD record
ord-45e54d57dc354f80acb93b9ba7dbc371
Source dataset
uspto-grants-2015_09
Patent number
US09139546B2

Reaction notes

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