HCID 58707319, compound → HCID 58707309, compound

HRID 1910628Notes

Reaction equation

HRID 1910628 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:13][Mg]Br>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([O:10][CH3:11])=[C:6]([CH:7]([OH:8])[CH3:13])[CH:9]=1

Participants

4

Reactant 2

HCID 58707319HCID 58707319, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58707309HCID 58707309, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-Fluoro-2-methoxy-3-methylbenzaldehyde (1.2 g, 7.13 mmol) in dry diethyl ether (20 mL) at 0° C. was added methylmagnesium bromide of 3.0 M in ether (6.0 mL, 17.83 mmol). The reaction mixture was brought to room temperature and was stirred for 30 min. then refluxed for 3 h. It was then cooled to 0° C. and quenched by adding saturated aqueous NH4Cl. The two liquid layers were separated. The aqueous layer was extracted with ether. The combined organic layers were washed with water, dried, and concentrated to the crude compound which was purified by silica gel column (10-25% ethyl acetate in hexanes) to afford 1-(5-fluoro-2-methoxy-3-methylphenyl)ethanol (1.0 g, 76%): 1H NMR (400 MHz, CDCl3): δ 7.12 (dd, 1H), 6.83 (dd, 1H), 4.72 (m, 1H), 3.81 (s, 3H), 2.38 (s, 3H), 1.47 (d, 3H).

Workup

  1. customwas brought to room temperature
  2. temperaturethen refluxed for 3 h
  3. customquenched
  4. additionby adding saturated aqueous NH4Cl
  5. customThe two liquid layers were separated
  6. extractionThe aqueous layer was extracted with ether
  7. washThe combined organic layers were washed with water
  8. customdried
  9. concentrationconcentrated to the crude compound which
  10. customwas purified by silica gel column (10-25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-77b91383e8ce4e978e61980aaa101481
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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