Water → 4-[1-(3,4-Dimethoxyphenoxy)-4-hydroxybutyl]benzonitrile

HRID 411143Notes

Reaction equation

HRID 411143 reaction equation
B.CSC.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[O:10][CH:11]([C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1)[CH2:12][CH:13]=[CH2:14].O.B1([O-])O[O:30]1.O.O.O.O.[Na+]>C1COCC1>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[O:10][CH:11]([C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1)[CH2:12][CH2:13][CH2:14][OH:30]

Participants

6

Reactant 4

HCID 962Water2×HCID 12423031(Dimethyl sulfide)trihydroboronHCID 218676894-[1-(3,4-Dimethoxyphenoxy)-3-butenyl]benzonitrileHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 218677264-[1-(3,4-Dimethoxyphenoxy)-4-hydroxybutyl]benzonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulfide complex (2 M in ether, 11 mL, 22 mmol) was added dropwise to a cooled (−5° C.) solution of 4-[1-(3,4-dimethoxyphenoxy)-3-butenyl]benzonitrile (from step (i) above; 17.6 g, 56.8 mmol) in dry THF (15 mL) over a period of 15 minutes (during which time the reaction temperature rose to 0° C.). The resulting mixture was stirred at between 0 and 10° C. for 1.5 h, before being allowed to warm to rt. Stirring was continued for a further 3.5 h at this temperature before water (22 mL) and sodium perborate tetrahydrate (11 g, 66 mmol) were added. The biphasic mixture was stirred for 2 h at rt before the water layer was separated and extracted with ether. The combined organic layers were washed with brine, dried and concentrated in vacuo. The resulting residue was purified by chromatography on silica gel, eluting with IPA:ethyl acetate:heptane (5:25:70) to yield 14.5 g (77%) of the sub-title compound.

Workup

  1. customrose to 0° C.
  2. stirringStirring
  3. additionwere added
  4. customwas separated
  5. extractionextracted with ether
  6. washThe combined organic layers were washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by chromatography on silica gel
  10. washeluting with IPA:ethyl acetate:heptane (5:25:70)

Sources & evidence

ORD record
ord-a304a75cb385486592cb80fd41eca0f6
Source dataset
uspto-grants-2003_05
Patent number
US06559143B1

Reaction notes

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