HCID 87212268, compound → HCID 25030275, compound

HRID 1364246Notes

Reaction equation

HRID 1364246 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.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[Mg]Br>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]([C:19]2[S:18][CH:22]=[CH:21][CH:20]=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 178418438HCID 178418438, compound

Product 1

HCID 25030275HCID 25030275, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The aldehyde 5 were dissolved in dry THF and cooled to −20° C. thiphen-2-yl magnesium 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 product was purified by flash chromatography using 20% EtOAc/Hexanes as the solvent system to obtain a white solid. Yield=82.4% (Rf=0.26; 20% EtOAc/Hexanes) 1H NMR, 500 MHz Varian, CDCl3, δ 7.31 (d, J=2 Hz, 1H), 7.29 (d, J=4.00 Hz, 1H), 7.12 (d, J=9.50 Hz, 2H), 6.99 (m, J=9.50 Hz, 2H), 6.75 (s, 2H), 6.08 (d, J=4.00, 1H), 3.73 (s, 3H), 2.37 (s, 3H), MS: m/z (ESI, pos.)=333.5 ([M+23])

Workup

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

Sources & evidence

ORD record
ord-dd90e2bdf2334d67a2c13c367de1d93e
Source dataset
uspto-grants-2011_02
Patent number
US07888365B2

Reaction notes

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