2-Chloroethanol → HCID 22170578, compound

HRID 1017571Notes

Reaction equation

HRID 1017571 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:13][CH2:14][CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:13][CH2:14][CH2:15][O:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 11776TriphenylphosphineHCID 39129Methyl 3-HydroxyphenylacetateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 22170578HCID 22170578, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-hydroxyphenylacetate (1.66 g, 10 mmol), 2-chloroethanol (1.34 mL, 2 eq.) and triphenylphosphine (5.24 g, 2 eq.) in THF (100 mL) at 0° C. was added dropwise diisopropylazodicarboxylate (3.96 mL, 2 eq.) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was then quenched with NaHCO3 and the product was extracted with EtOAc. The EtOAc layers were washed with brinebrine, dried over sodium sulfate, and concentrated. Purification on a silica gel column with 10% EtOAc in hexane gave methyl 3-(2-chloroethyloxy)phenylacetate (1.6 g, 70% yield) which was converted to 3-(1-methylindol-3-yl)-4-[3-(2-aminoethyloxy)phenyl]-1H-pyrrole-2,5-dione by following the procedure described in Example 5, Steps 2-6 above.

Workup

  1. customThe reaction mixture was then quenched with NaHCO3
  2. extractionthe product was extracted with EtOAc
  3. washThe EtOAc layers were washed with brinebrine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification on a silica gel column with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-5f0eca7da55e46c68f71bf5110761035
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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