Water → 4-Benzyloxy-5-(4-fluorophenoxy)-1-pentanol

HRID 2083309Notes

Reaction equation

HRID 2083309 reaction equation
[CH2:1]([O:8][CH:9]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:10][CH:11]=[CH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].B(F)(F)F.CC[O:30]CC.O>O1CCCC1>[CH2:1]([O:8][CH:9]([CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)[CH2:10][CH2:11][CH2:12][OH:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 213176584-Benzyloxy-5-(4-fluorophenoxy)-1-pentene

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-benzyloxy-5-(4-fluorophenoxy)-1-pentene (2.86 g., 10 mmoles), sodium borohydride (0.47 g., 12.5 mmoles), and tetrahydrofuran (25 ml.) is added dropwise a solution of boron fluoride etherate (2.1 ml., 16.7 mmoles) in tetrahydrofuran (5 ml.) at ice-bath temperatures under a nitrogen atmosphere. The resulting mixture is further stirred at room temperature overnight (ca. 15 hours). The reaction flask is chilled in an ice bath and water (2 ml.) is very cautiously added to destroy the excess hydride, followed by the additions of sodium hydroxide (5N, 4ml.) and hydrogen peroxide (30%, 8 ml.). The final mixture is stirred at room temperature for one half hour, diluted with cold water and then extracted with chloroform three times. The combined extracts are washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent is evaporated in vacuo leaving the title compound as a viscous oil (3.00 g., 10 mmoles, 100%). ir (neat) 2.97, 3.30, 3.41, 6.22, 6.68, 6.90, 8.03, 8.30, 9.16, 9.44, 12.10, 13.20, 13.60, 14.40μ; pmr (CCl4)δ1.4-1.9 (4H, m), 3.2-4.2 (6H, m), 4.58 (2H, broad s), 6.6-7.1 (4H, m), 7.20 (5H, s).

Workup

  1. temperatureThe reaction flask is chilled in an ice bath
  2. customto destroy the excess hydride
  3. stirringThe final mixture is stirred at room temperature for one half hour
  4. additiondiluted with cold water
  5. extractionextracted with chloroform three times
  6. washThe combined extracts are washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-a85ef28b87e1448bbf4b4a50abb32f26
Source dataset
uspto-grants-1978_04
Patent number
US04085125

Reaction notes

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