99113-85-6 → HCID 67268960, compound

HRID 251740Notes

Reaction equation

HRID 251740 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[O:13])[O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1>[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]([OH:13])[CH2:12][CH2:9][CH2:8][CH2:7][CH2:1][CH:2]=[CH2:3])[O:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 1354168999113-85-6

Product 1

HCID 67268960HCID 67268960, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The resulting Grignard solution was added to a solution of 4-phenyl-2-furaldehyde (1 eq.) in THF at 0° C. under Ar and the mixture was stirred for 30 min. The reaction was quenched by slow addition of sat. aq. NH4Cl solution and the desired product was extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude was purified by column chromatography eluting with 5% EtOAc/Petroleum ether to afford the desired alcohol. 1H NMR (300 MHz, CD3Cl3) δ: 7.65 (2H, d, J=7.3 Hz), 7.42 (2H, t, J=7.2 Hz), 7.25-7.15 (1H, m), 6.60 (1H, d, J=5.3 Hz), 6.30 (1H, d, J=5.3 Hz), 5.87-5.75 (1H, m), 5.05-4.89 (2H, m), 4.75-4.65 (1H, m), 2.15-2.05 (2H, m), 1.87-1.75 (2H, m), 1.45-1.35 (6H, m). MS (ES) C18H22O2 requires: 270 found: 271 (M+H)+.

Workup

  1. customThe reaction was quenched by slow addition of sat. aq. NH4Cl solution
  2. extractionthe desired product was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by column chromatography
  7. washeluting with 5% EtOAc/Petroleum ether

Sources & evidence

ORD record
ord-9176b2c73d3448aa83c9a842f7ed39fb
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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