Tetrahydrofuran → 1-(3,4-Difluorophenyl)-1-propanol

HRID 1167710Notes

Reaction equation

HRID 1167710 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6].[CH2:11]([Mg]Br)[CH3:12].C1COCC1.CCCCCC.CCOC(C)=O>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH2:11][CH3:12])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 5880883,4-DifluorobenzaldehydeHCID 21226206Ethyl acetate hexaneHCID 178418443HCID 178418443, compound

Product 1

HCID 225984421-(3,4-Difluorophenyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,4-difluorobenzaldehyde (5.0 g, 35.2 mmol) in diethyl ether (35 mL)in a round bottom flask was added a solution of ethylmagnesium bromide in THF (38.0 mL, 38.0 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h when TLC analysis indicated that the reaction was complete (Rf=0.5, 8:1 hexane/EtOAc). The reaction was quenched carefully by adding 38 mL of water. It was extracted with diethyl ether (2×30 mL), washed with brine and the organic layer was dried over Na2SO4. The solvent was removed in vacuo after filtration and 1-(3,4-difluorophenyl)propan-1-ol was obtained as a yellow oil (crude wt.=6.0 g) which looked >90% pure by NMR. It was used in the next step without purification.

Workup

  1. customThe reaction was quenched carefully
  2. additionby adding 38 mL of water
  3. extractionIt was extracted with diethyl ether (2×30 mL)
  4. washwashed with brine
  5. dry with materialthe organic layer was dried over Na2SO4
  6. customThe solvent was removed in vacuo
  7. filtrationafter filtration

Sources & evidence

ORD record
ord-dbb77915ee6849f6ab1bf8ee67363b7f
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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