Ammonium Chloride → HCID 66717153, compound

HRID 1994602Notes

Reaction equation

HRID 1994602 reaction equation
[CH3:1][Mg]Cl.[F:4][C:5]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[C:15](=[O:17])[CH3:16].[NH4+].[Cl-]>CCCCCCC.C1COCC1>[F:4][C:5]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[C:15]([OH:17])([CH3:1])[CH3:16]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 10104179HCID 10104179, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 66717153HCID 66717153, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

A solution of methylmagnesium chloride (3M in THF, 1.74 mL, 5.22 mmol) was added dropwise to a stirred solution of 1-(2-fluoro-3,4-dimethoxyphenyl)ethanone (J. Chem. Soc. Perkin Trans. 2 1994, 547-555) (646 mg, 3.26 mmol) in heptane (3.1 mL) and THF (1.4 mL) at −20° C. under N2. The reaction was allowed to warm to room temperature and was stirred for 4 h. 50% Saturated NH4Cl (20 mL) was added and the mixture was extracted with EtOAc (3×20 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give 2-(2-fluoro-3,4-dimethoxyphenyl)propan-2-ol as a colorless oil. LCMS calc.=197.1; found=197.1 (M-OH)+. 1H NMR (600 MHz, CDCl3) δ 7.14 (t, J=8.8 Hz, 1H), 6.61 (dd, J=8.8, 1.4 Hz, 1H), 3.86 (s, 3H), 3.83 (s, 3H), 2.56-2.25 (br s, 1H), 1.58 (s, 6H).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×20 mL)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d25a9428520b40e9b4d92993d1c0953e
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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