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Triphenylphosphine → 1-(1-Cyclopropylethoxy)-2,5-dimethyl-4-nitrobenzene

HRID 626316
Notes
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Reaction equation

HRID 626316 reaction equation
N(C(OCCOC)=O)=NC(OCCOC)=O.[CH3:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[C:21]([CH3:27])=[CH:20][C:19]=1[OH:28].[CH:29]1([CH:32](O)[CH3:33])[CH2:31][CH2:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH:29]1([CH:32]([O:28][C:19]2[CH:20]=[C:21]([CH3:27])[C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:18]=2[CH3:17])[CH3:33])[CH2:31][CH2:30]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 791041-CyclopropylethanolHCID 2821102,5-Dimethyl-4-nitrophenolHCID 516892Sodium BicarbonateHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamate

Product 1

HCID 1176205911-(1-Cyclopropylethoxy)-2,5-dimethyl-4-nitrobenzene
Yield 45.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

3.10 g of Bis(2-methoxyethyl) azodicarboxylate was added to a mixture of 1.70 g of 2,5-dimethyl-4-nitrophenol, 0.88 g of (1-cyclopropyl) ethanol, 3.20 g of triphenylphosphine and 100 mL of toluene at 0° C., and the mixture was stirred at 80° C. for 4 hours. After cooling, a saturated aqueous sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate, and then the organic layer was washed with water and saturated salt water and dried over anhydrous magnesium sulfate. The resulting residue was subjected to silica gel column chromatography to obtain 1.09 g of 1-(1-cyclopropylethoxy)-2,5-dimethyl-4-nitrobenzene.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated salt water
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-81d80c4b3eb749bbb8ca63be0e8bf261
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309191B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes