Hydrogen Peroxide → 4-Benzyloxy-5-(4-fluorophenoxy)-1-pentanol

HRID 867097Notes

Reaction equation

HRID 867097 reaction equation
[B].[CH2:2]([O:9][CH:10]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH2:11][CH:12]=[CH2:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+].[OH-:25].[Na+].OO>O1CCCC1.O>[CH2:2]([O:9][CH:10]([CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)[CH2:11][CH2:12][CH2:13][OH:25])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 5462311BoronHCID 213176584-Benzyloxy-5-(4-fluorophenoxy)-1-pentene

Product 1

HCID 213175844-Benzyloxy-5-(4-fluorophenoxy)-1-pentanolYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of boron trifluoroide.etherate (2.1 ml., 16.7 millimole) in dry tetrahydrofuran (15 ml.) is added dropwise to a stirred mixture of 4-benzyloxy-5-(4-fluorophenoxy)-1-pentene (2.86 g., 10 millimole) and sodium borohydride (0.47 g., 12.5 millimole) in dry tetrahydrofuran (25 ml.) maintained at 0°-5° C. under a nitrogen atmosphere. The resulting reaction mixture is warmed to 25° C. and maintained at 25° C. for 15 hours. After cooling to 0°-5° C., the reaction mixture is treated cautiously via successive dropwise additions of water (2 ml.), 5 N sodium hydroxide (4 ml.) and 30% hydrogen peroxide (8 ml.). After stirring at 25° C. for 1/2 hour, the resulting mixture is diluted with ice water and extracted with chloroform three times. The combined organic extract is washed with saturated aqueous brine, dried over magnesium sulfate, and filtered. Evaporation of the filtrate in vacuo provides the title compound as a viscous oil (3.0 g., 100%); pmr (CCl4) δ1.4-1.9 (4 H, m), 3.2-4.2 (6H, m), 4.58 (2H, broad s), 6.6-7.1 (4H, m) and 7.20 (5H, s).

Workup

  1. temperaturemaintained at 0°-5° C. under a nitrogen atmosphere
  2. customThe resulting reaction mixture
  3. temperaturemaintained at 25° C. for 15 hours
  4. temperatureAfter cooling to 0°-5° C.
  5. extractionextracted with chloroform three times
  6. extractionThe combined organic extract
  7. washis washed with saturated aqueous brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customEvaporation of the filtrate in vacuo

Sources & evidence

ORD record
ord-2b9968aa44d1443ab6e18951a85d4e98
Source dataset
uspto-grants-1978_07
Patent number
US04102888

Reaction notes

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