Ethyl Acetate → HCID 53951647, compound

HRID 862091Notes

Reaction equation

HRID 862091 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[C:10]([F:25])=[CH:11][C:12]([O:21][CH2:22][O:23][CH3:24])=[C:13]([CH:20]=1)[C:14](OCOC)=[O:15])#[N:8].C(OCC)(=O)C>C(OCC)C.[Cl-].[Na+].O>[C:7]([C:9]1[C:10]([F:25])=[CH:11][C:12]([O:21][CH2:22][O:23][CH3:24])=[C:13]([CH:20]=1)[CH2:14][OH:15])#[N:8]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 19701630HCID 19701630, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 53951647HCID 53951647, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Lithium aluminum hydride (2.39 g) was added portionwise to a solution of methoxymethyl 5-cyano-4-fluoro-2-methoxymethoxybenzoate (16.6 g) in diethyl ether (500 ml) at -30° C., and the mixture was stirred for 30 minutes. The reaction mixture was poured into a saturated brine, to which was added ethyl acetate, followed by filtration through celite. The organic layer was washed with a saturated brine, dried (anhydrous magnesium sulfate), and concentrated. The residue was chromatographed on silica gel using ethyl 10 acetate/hexane as eluent to give 5-cyano-4-fluoro-2-methoxymethoxybenzyl alcohol (10.0 g) (Compound B-49). The physical properties are shown in Table 8.

Workup

  1. filtrationfollowed by filtration through celite
  2. washThe organic layer was washed with a saturated brine
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-110e3ae81aeb489dbd14d7444f082cbd
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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