Triphenylphosphine → HCID 117620575, compound

HRID 626318Notes

Reaction equation

HRID 626318 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].[CH3:29][C:30]1([CH3:37])[C:32]([CH3:34])([CH3:33])[CH:31]1[CH2:35]O.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>[CH3:17][C:18]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[C:21]([CH3:27])=[CH:20][C:19]=1[O:28][CH2:35][CH:31]1[C:32]([CH3:34])([CH3:33])[C:30]1([CH3:37])[CH3:29]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 2821102,5-Dimethyl-4-nitrophenolHCID 516892Sodium BicarbonateHCID 5441792,2,3,3-TetramethylcyclopropanemethanolHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamate

Product 1

HCID 117620575HCID 117620575, compoundYield 8.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

1.97 g of Bis(2-methoxyethyl) azodicarboxylate was added to a mixture of 1.08 g of 2,5-dimethyl-4-nitrophenol, 0.83 g of (2,2,3,3-tetramethylcyclopropyl)methanol, 2.04 g of triphenylphosphine and 100 mL of toluene at 0° C., and the mixture was stirred at 90° 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 0.15 g of 2,5-dimethyl-4-nitro-1-[(2,2,3,3-tetramethylcyclopropyl) methoxy]benzene.

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-23c8524c408f49c9a356b4fac06ecd9e
Source dataset
uspto-grants-2016_04
Patent number
US09309191B2

Reaction notes

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