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

HRID 19531

Reaction equation

HRID 19531 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.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.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

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 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 506%

Reagents, catalysts & solvents 1

HCID 22633675Benzene tetrahydrofuranSolvent

Procedure

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (2 g, 6.79 mmol) prepared in Preparation Example 2 was dissolved in THF/benzene (270 mL/90 mL) solution, and 2-hydroxyethylmorpholine (5.83 g, 44.45 mmol) and triphenylphosphine (11.66 g, 44.45 mmol) were added thereto and kept at 0° C. Diisopropyl azodicarboxylate (8.99 g, 44.45 mmol) was added dropwise to the mixture, followed by stirring for 2 hrs at room temperature. The resulting mixture washed with saturated saline and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 14 g of the titled compound (yield: 93%) as a red solid.

Workup

  1. additionwere added
  2. customkept at 0° C
  3. washThe resulting mixture washed with saturated saline
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under a reduced pressure
  8. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7e1aa80291fd4e768440584087e33e45
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Linked notes

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