HCID 13189248, compound → 4-(1-Ethoxyethoxy)-3,3-difluoro-4-methylpentan-1-ol

HRID 905013Notes

Reaction equation

HRID 905013 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][CH2:11][CH2:12][C:13]([F:24])([F:23])[C:14]([O:17][CH:18]([O:20][CH2:21][CH3:22])[CH3:19])([CH3:16])[CH3:15])(=O)C>CCOCC>[CH2:21]([O:20][CH:18]([O:17][C:14]([CH3:16])([CH3:15])[C:13]([F:23])([F:24])[CH2:12][CH2:11][OH:10])[CH3:19])[CH3:22]

Participants

4

Reactant 2

HCID 13189248HCID 13189248, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 131892494-(1-Ethoxyethoxy)-3,3-difluoro-4-methylpentan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
35 °C

Procedure

To a mixture of 2.25 g (0.059 mol) of lithium aluminum hydride in 50 mL of ether at 0° C. was added dropwise, 11.30 g (0.040 mol) of 4-(1-ethoxyethoxy)-3,3-difluoro-4-methyl-1-pentanol 1-acetate in 130 mL of ether. The mixture was heated at reflux (35° C.) for 3 hr and then was recooled to 0° C. The mixture was quenched by adding dropwise 4.5 mL of water followed by 3.6 mL of 10% aqueous sodium hydroxide. The mixture was stirred at 25° C. for 0.5 hr and was filtered. Evaporation of solvent and column chromatography of the residue on 0.06-0.20 mm silica gel afforded 4-(1-ethoxyethoxy)-3,3-difluoro-4-methyl-1-pentanol. NMR (CDCl3) δ5.00 (quartet, 1, J=7 Hz), 3.86 (broad, 2), 3.51 (quartet, 2, J=7 Hz), 2.25 (multiplet, 2), 1.35 (triplet, 6, J=1 Hz), 1.30 (doublet, 3, J=7 Hz), and 1.18 ppm (triplet, 3, J=7 Hz).

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was heated
  3. customwas recooled to 0° C
  4. customThe mixture was quenched
  5. additionby adding dropwise 4.5 mL of water
  6. filtrationwas filtered
  7. customEvaporation of solvent and column chromatography of the residue on 0.06-0.20 mm silica gel

Sources & evidence

ORD record
ord-85e6cd2a35074ee7b0f46ce471fa78fa
Source dataset
uspto-grants-1983_12
Patent number
US04421690

Reaction notes

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