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

HRID 1833479Notes

Reaction equation

HRID 1833479 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, 4 ml.) 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-39a1f5ec1c93461d8334157f0165df08
Source dataset
uspto-grants-1978_01
Patent number
US04066675

Reaction notes

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