Hydrochloric Acid → HCID 54474777, compound

HRID 260640Notes

Reaction equation

HRID 260640 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][CH2:11][Si:12]([CH3:22])([CH3:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)(=O)C.C(OC(=O)C)C.Cl>C(OCC)C.O>[CH3:21][Si:12]([CH3:22])([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[CH2:11][OH:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 17991909HCID 17991909, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54474777HCID 54474777, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

To a mixture of lithium aluminum hydride (0.06 g, 1.58 mmol) in diethyl ether (5 ml) is added dropwise acetoxymethyldimethyl-3-fluorobenzylsilane (0.38 g, 1.58 mmol) in diethyl ether (2 ml). The mixture is then allowed to react for 0.5 hours at room temperature, treated with ethylacetate (2 ml), hydrolyzed with 1N HCl (6.5 ml), and poured into water (20 ml) and diethyl ether (10 ml). The organic layer is washed with water, brine, dried over MgSO4 and the solvent removed in vacuo. Chromatography (silica gel, hexane/ether-60/40 affords the title compound (0.23 g, 73% yield).

Workup

  1. customto react for 0.5 hours at room temperature
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over MgSO4
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ff1efa266efb48f2bf48104ba04dec7d
Source dataset
uspto-grants-1996_06
Patent number
US05529988

Reaction notes

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