Cyclopentanol → 2-Cyclopentyloxy-4-methoxy-benzonitrile

HRID 1582480Notes

Reaction equation

HRID 1582480 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>C1COCC1>[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 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-hydroxy-4-methoxy-benzonitrile (90 mg, 0.60 mmol, example 9), cyclopentanol (55 mg, 0.64 mmol) and triphenylphosphine (167 mg, 0.64 mmol) in THF (3 mL) at −78° C. was added diethyl azodicarboxalate (0.16 mL, 0.860 mmol, 85%). 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, 90%).

Workup

  1. customThe cooling bath was removed
  2. 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)
  3. washeluting with 0-8% diethyl ether in hexanes

Sources & evidence

ORD record
ord-e66ebacc89a543a9934e553575281a43
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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