Water → 4-{4-Hydroxy-1-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl}-benzonitrile

HRID 411538Notes

Reaction equation

HRID 411538 reaction equation
B.CSC.[O:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][C:12]1[CH:30]=[CH:29][C:15]([O:16][CH:17]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[CH2:18][CH:19]=[CH2:20])=[CH:14][CH:13]=1.O.CC[O:34]CC>C1COCC1>[OH:34][CH2:20][CH2:19][CH2:18][CH:17]([C:21]1[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=1)[O:16][C:15]1[CH:29]=[CH:30][C:12]([O:11][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][O:5]2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 12423031(Dimethyl sulfide)trihydroboronHCID 222356714-{1-[4-(Tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile

Product 1

HCID 222354084-{4-Hydroxy-1-[4-(tetrahydro-2h-pyran-2-yloxy)phenoxy]butyl}-benzonitrileYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethylsulfide complex (3.5 mL of 2 M in ether, 7 mmol) was added dropwise to a cooled (5° C.) solution of 4-{1-[4-(tetrahydro-2H-pyran-2-yloxy)phenoxy]-3-butenyl}benzonitrile (see step (i) above; 4.6 g, 13 mmol) in dry THF over a period of 15 min. The resulting mixture was stirred at between 0 and 5° C. for 1.5 h. Stirring was then continued for a further 4 h at rt. Water (14 mL) and NaBO3 (5 g) were added and the mixture stirred overnight. Ether was added and the resulting organic layer was separated, washed with water and brine, dried and then evaporated. The resulting residue was purified by chromatography on silica gel, eluting with IPA:EtOAc:heptane (5:20:70), to give 2.44 g (58%) of the sub-title compound.

Workup

  1. stirringStirring
  2. waitwas then continued for a further 4 h at rt
  3. stirringthe mixture stirred overnight
  4. customthe resulting organic layer was separated
  5. washwashed with water and brine
  6. customdried
  7. customevaporated
  8. customThe resulting residue was purified by chromatography on silica gel
  9. washeluting with IPA:EtOAc:heptane (5:20:70)

Sources & evidence

ORD record
ord-a7c7ce7d0bff421ebc4c7b1491249170
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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