Triphenylphosphine → HCID 68785453, compound

HRID 1519778Notes

Reaction equation

HRID 1519778 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[N:13]1([CH2:18][CH2:19]O)[CH:17]=[CH:16][N:15]=[CH:14]1.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.CCOC(C)=O.O>[N:13]1([CH2:18][CH2:19][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 74168N-(2-Hydroxyethyl)imidazoleHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 68785453HCID 68785453, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring mixture of the methyl 2-(4-hydroxyphenyl)acetate (1.4 g, 1 EQ) and 2-(1H-imidazol-1-yl)ethanol (1.0 g) in THF (0.5 mL, 0.5 M) at 0° C. was added PPh3 (2.9 g). To this mixture was added dropwise DIAD (2.2 mL) over 10 min. The reaction mixture was warmed to ambient temperature overnight. A normal aqueous workup with water and EtOAc was followed. The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified via silica gel chromatography to give methyl 2-(4-(2-(1H-imidazol-1-yl)ethoxy)phenyl)acetate. Method[1], MS(ESI) 261.1, Retention time=0.782 min.

Workup

  1. dry with materialThe organic layers were dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-776af39cd1844fe09c665f697eb7fce9
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

Loading…