Triphenylphosphine → 6-(2-morpholine-4-ylethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 17878

Reaction equation

HRID 17878 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([OH:21])[CH:9]=2)=[O:5])[CH3:2].O[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.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>O1CCCC1.C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)[CH:9]=2)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 5363146Diisopropyl azodicarboxylateHCID 118452796-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 686975066-(2-morpholine-4-ylethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 128.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl ester [compound of formula (II)] (10.90 g, 26.75 mmol) prepared in Step 4 of Example 1 was dissolved in tetrahydrofuran:benzene (270 ml:90 ml). Then, 4-(2-hydroxyethyl)morpholine (5.83 g, 44.45 mmol) and triphenylphosphine (11.66 g, 44.45 mmol) were added thereto. Diisopropylazodicarboxylate (8.99 g, 44.45 mmol) was added dropwise to the mixture at 0° C., and stirred for 2 hours at room temperature. The reaction mixture was washed with saturated sodium chloride and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate) to obtain the title compound (14 g, yield 93%) as a red solid.

Workup

  1. washThe reaction mixture was washed with saturated sodium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe resulting residue was purified by column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-15e7e97f2190444b81dac61e944a6d96
Source dataset
uspto-grants-2010_06
Patent number
US07741323B2

Linked notes

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