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

HRID 17875

반응식

HRID 17875 반응식
[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].[C:23]1([CH2:29][CH2:30][CH2:31]O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[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][CH2:31][CH2:30][CH2:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:9]=2)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 31234BenzenepropanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 118452796-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

생성물 1

HCID 118452821-oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic acid ethyl ester수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl ester (1.7 g, 6.07 mmol), 3-phenylpropanol (1.65 g, 12.14 mmol) and triphenylphosphine (3.18 g, 12.14 mmol) were dissolved in tetrahydrofuran (100 ml). Diethyl azodicarboxylate (2 ml, 12.14 mmol) dissolved in tetrahydrofuran (20 ml) was added dropwise thereto at 0° C. After stirring for 6 hours at room temperature, the mixture was washed with brine, extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, the concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (diethyl ether:hexane=1:10) to obtain the title compound (yield 85%) as a dark red solid.

후처리

  1. additionwas added dropwise
  2. customat 0° C
  3. washthe mixture was washed with brine
  4. extractionextracted with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. concentrationthe concentrated under a reduced pressure
  7. customthe residue was purified by silica gel column chromatography (diethyl ether:hexane=1:10)

출처 및 근거

ORD 기록
ord-b01a65d8d7f7470f9c3b2f407b55bba8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741323B2

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