Triphenylphosphine → 2-(4-(3-Cyclopentylpropoxy)-3-methoxyphenyl)acetonitrile

HRID 925127

Reaction equation

HRID 925127 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[O:11][CH3:12].[CH:13]1([CH2:18][CH2:19][CH2:20]O)[CH2:17][CH2:16][CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH:13]1([CH2:18][CH2:19][CH2:20][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=2[O:11][CH3:12])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 69842CyclopentanepropanolHCID 782204-Hydroxy-3-methoxyphenylacetonitrileHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 1183893652-(4-(3-Cyclopentylpropoxy)-3-methoxyphenyl)acetonitrileYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-Hydroxy-3-methoxyphenyl)acetonitrile (0.54 g, 3.31 mmol) in THF (10 mL) was treated with 3-cyclopentylpropan-1-ol (0.424 g, 3.31 mmol), triphenylphosphine (1.128 g, 4.3 mmol) and cooled in an ice bath to 0° C. DIAD (0.785 ml, 4 mmol) was added to the reaction mixture dropwise over the period of 5 min, and the reaction was left stirring slowly warming to room temperature over 18 hours. The reaction mixture was concentrated. Purification by flash chromatography (silica gel, 0-40% EtOAc/hexanes) afforded 0.871 g (96%) of 2-(4-(3-cyclopentylpropoxy)-3-methoxyphenyl)acetonitrile. MS (ESI) m/z 274 (M+H)+

Workup

  1. waitthe reaction was left
  2. temperaturewarming to room temperature over 18 hours
  3. concentrationThe reaction mixture was concentrated
  4. customPurification by flash chromatography (silica gel, 0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f40af98d19064883b29c457bc30d1125
Source dataset
uspto-grants-2016_03
Patent number
US09284272B2

Linked notes

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