Methanol → HCID 68703601, compound

HRID 2244326Notes

Reaction equation

HRID 2244326 reaction equation
Cl[C:2]1(Cl)[CH2:4][C:3]1([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[F:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].CO>C1COCC1.C(OCC)(=O)C>[F:5][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[CH2:2][CH2:4]1

Participants

7

Reactant 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride2×HCID 687008961-(2,2-Dichloro-1-fluorocyclopropyl)-4-methylbenzene

Product 1

HCID 68703601HCID 68703601, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(2,2-dichloro-1-fluoro-cyclopropyl)-4-methyl-benzene (1.18 g, 5.39 mmol) in THF (10 mL) was added at 0° C. to a suspension of lithium aluminum hydride (1.64 g, 43.1 mmol) in THF. The reaction mixture was stirred for 16 h at RT, then another portion of lithium aluminum hydride (613 mg, 16.1 mmol) was added, then after 3 h, 1 M aq. potassium sodium tartrate solution, methanol and ethyl acetate were added. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane) afforded the title compound (702 mg, 87%). Colourless liquid, MS (EI) 150.1 (M+).

Workup

  1. waitafter 3 h
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-d0014ce5ce7a4e52938c1bf911422fa0
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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