HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 17875
Notes
Print preview

Reaction equation

HRID 17875 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].[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b01a65d8d7f7470f9c3b2f407b55bba8
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741323B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes