Tetrahydrofuran → 4-((4-Fluorophenyl)(hydroxy)methyl)benzaldehyde

HRID 710318Notes

Reaction equation

HRID 710318 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[CH2:10]1[CH2:14][O:13][CH2:12][CH2:11]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:12]([OH:13])[C:11]2[CH:10]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:14]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 178418676HCID 178418676, compound

Product 1

HCID 113682014-((4-Fluorophenyl)(hydroxy)methyl)benzaldehydeYield 27%

Procedure

To a stirred solution of terepathaldehyde (0.5 g, 3.7 mmol) in anhydrous THF (8 ml) at 0° C. was added 2M THF solution of 4-fluorophenyl magnesium bromide (1.86 ml; 3.72 mmol) drop wise and the mixture was allowed to warm up to room temperature and stirred for 4 h. The mixture was then quenched with NH4Cl solution and diluted with to 100 ml with EtOAc. The organic layer was washed with H2O, dried over MgSO4, filtered and the filtrate evaporated to dryness. The residue was purified by FCC (SiO2) to give the desired product (0.23 g; 27%) as creamy paste. 1H-NMR (CDCl3) 2.57 (s, 1H); 5.86 (s, 1H); 7.0 (tr, 2H, J=8.58 Hz); 7.28-7.33 (m, 2H); 7.51 (d, 2H, J=7.98 Hz); 7.81 (d, 2H, J=8.1 Hz); 9.95 (s, 1H).

Workup

  1. customThe mixture was then quenched with NH4Cl solution
  2. additiondiluted with to 100 ml with EtOAc
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe filtrate evaporated to dryness
  7. customThe residue was purified by FCC (SiO2)

Sources & evidence

ORD record
ord-e9dd9f0768ec4ee1aae41ca534b5b0fd
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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