Triphenylphosphine → HCID 20779195, compound

HRID 2179937Notes

Reaction equation

HRID 2179937 reaction equation
[Cl:1][CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15](O)[CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([O:5][C@@H:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:3][CH2:2][Cl:1])[CH:14]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanolHCID 34427894-Chloro-2-hydroxybenzonitrile

Product 1

HCID 20779195HCID 20779195, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-α-(2-Chloroethyl)benzenemethanol (170 mg, 1.0 mmol), 4-chloro-2-hydroxybenzonitrile (154 mg, 1.0 mmol.) and triphenylphosphine (260 mg, 1.0 mmol.) in dry tetrahydrofuran (5 ml) were stirred in an ice bath under nitrogen whilst diethyl azodicarboxylate (0.16 ml, 1.0 mmol.) was added. The reaction mixture was allowed to warn to room temperature and stirred for 3 days. The solvent was evaporated and the residue dissolved in toluene, added to the top of a flash chromatography column and eluted with 10% ether/isohexane to give the product (220 mg, 72%) as a viscous oil.

Workup

  1. additionwas added
  2. customto warn to room temperature
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in toluene
  5. additionadded to the top of a flash chromatography column
  6. washeluted with 10% ether/isohexane

Sources & evidence

ORD record
ord-4a613e2188d7442099fbdecf70ecbe71
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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