Triphenylphosphine → HCID 69743753, compound

HRID 2183858Notes

Reaction equation

HRID 2183858 reaction equation
CC(C)(OC([NH:7][CH2:8][CH2:9][C@H:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12])=O)C.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([OH:26])[CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:10]([OH:15])(=[O:26])[C:11]([OH:13])=[O:12].[NH2:7][CH2:8][CH2:9][C@@H:10]([O:15][C:24]1[CH:25]=[C:18]([Cl:17])[CH:19]=[CH:20][C:21]=1[C:22]#[N:23])[CH2:11][O:13][CH3:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 34427894-Chloro-2-hydroxybenzonitrileHCID 54753949HCID 54753949, compound

Product 1

HCID 69743753HCID 69743753, compoundYield 148.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The product of step (b) (3.25 g, 13.9 mmol), 4-chloro-2-hydroxybenzonitrile (2.14 g, 13.9 mmol) and triphenylphosphine (4.38 g, 16.7 mmol) were dissolved in anhydrous tetrahydrofuran (80 ml) and the solution cooled to 0° C. Diethyl azodicarboxylate (2.91 g, 16.7 mmol) was added dropwise and the solution allowed to warm to room temperature, then stirred for 2 days. The solvent was removed in vacuo and the residue chromatographed on flash silica, eluting with hexane:ethyl acetate (3:1), to afford the title compound as a white solid (3.562 g, 69%).

Workup

  1. temperatureto warm to room temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue chromatographed on flash silica
  4. washeluting with hexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-74d785a9db304a8a84684f86bf9ee236
Source dataset
uspto-grants-2005_05
Patent number
US06900243B2

Reaction notes

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