Triphenylphosphine → (R)-(-)-2-(1Methylheptyloxy)benzonitrile

HRID 651304Notes

Reaction equation

HRID 651304 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][C@H:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COC(OC1C=CC(C2C=CC(C(OCCCCCCCC)=O)=CC=2)=CC=1)=O>>[CH3:10][C@@H:11]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 5

HCID 11776TriphenylphosphineHCID 119072-HydroxybenzonitrileHCID 2723888(+)-2-OctanolHCID 5462977Diethyl azodicarboxylateHCID 18328376Octyl4'-methoxycarbonyloxy-4-biphenylcarboxylate

Product 1

HCID 21308782(R)-(-)-2-(1Methylheptyloxy)benzonitrile

Procedure

Quantities: 2-(hydroxybenzonitrile (38) (9.17 g, 0.077 mol), (S)-(+)-octan-2-ol (10.00 g, 0.077 mol), DEAD (13.41 g, 0.077 mol), triphenylphosphine (20.20 g, 0.077 mol). The experimental procedure was as described for the preparation of compound 5. The crude product was purified by column chromatography (20% petrol/dichloromethane) to give a colourless oil.

Workup

  1. customThe crude product was purified by column chromatography (20% petrol/dichloromethane)
  2. customto give a colourless oil

Sources & evidence

ORD record
ord-d3166a0e53b245d29c56fc1a0ebda336
Source dataset
uspto-grants-2001_08
Patent number
US06278028B1

Reaction notes

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