3-Pentanol → HCID 58404508, compound

HRID 1172916Notes

Reaction equation

HRID 1172916 reaction equation
[CH3:1][CH2:2][CH:3](O)[CH2:4][CH3:5].[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[OH:16])[C:11]#[N:12].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH:3]([CH2:4][CH3:5])[CH2:2][CH3:1])[C:11]#[N:12]

Participants

6

Reactant 4

HCID 114283-PentanolHCID 11776TriphenylphosphineHCID 2735739Benzonitrile, 3-chloro-4-hydroxy-HCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 58404508HCID 58404508, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Into a scintillation vial containing a solution of pentan-3-ol (22 mg, 0.25 mmol) dissolved in THF (2 mL) was added a solution of 3-chloro-4-hydroxy-benzonitrile (38 mg, 0.25 mmol) in THF (2 mL) followed by PS-PPh3 resin (357 mg, 0.5 mmol, loading 1.4 mmol/g) and a solution of DIAD (76 mg, 0.375 mmol) in THF (2 mL). The vial was capped and shaken at room temperature overnight. The reaction mixture was filtered and the resin was washed with THF (4 mL). The filtrate was concentrated to dryness to give 3-chloro-4-(1-ethyl-propoxy)-benzonitrile.

Workup

  1. customThe vial was capped
  2. filtrationThe reaction mixture was filtered
  3. washthe resin was washed with THF (4 mL)
  4. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-1d140ac4affc4179b47e787e892d98dc
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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