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

HRID 17878

反応式

HRID 17878 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-15e7e97f2190444b81dac61e944a6d96
出典データセット
uspto-grants-2010_06
特許番号
US07741323B2

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