Cyclopentanol → 2-Cyclopentyloxy-4-methoxy-benzonitrile

HRID 1167314Notes

Reaction equation

HRID 1167314 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:12]1(O)[CH2:16][CH2:15][CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:12]1([O:1][C:2]2[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 114236802-Hydroxy-4-methoxybenzonitrile

Product 1

HCID 227211652-Cyclopentyloxy-4-methoxy-benzonitrileYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-hydroxy-4-methoxy-benzonitrile (90 mg, 0.573 mmol), cyclopentanol (55 mg, 0.630 mmol) and triphenylphosphine (167 mg, 0.630 mmol) in tetrahydrofuran (3 mL) cooled to −78° was added diethylazodicarboxalate (0.16 mL, 0.860 mmol). The cooling bath was removed and the reaction was allowed to warm up to room temperature over 1.5 h. The reaction mixture was concentrated in vacuo, and purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 0-8% diethyl ether in hexanes yielded 2-cyclopentyloxy-4-methoxy-benzonitrile as a clear liquid (125 mg, 96%).

Workup

  1. additionwas added diethylazodicarboxalate (0.16 mL, 0.860 mmol)
  2. customThe cooling bath was removed
  3. concentrationThe reaction mixture was concentrated in vacuo, and purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  4. washeluting with 0-8% diethyl ether in hexanes

Sources & evidence

ORD record
ord-89c21a658c1942c593f40916d60090c0
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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