Triphenylphosphine → HCID 90032873, compound

HRID 2200125Notes

Reaction equation

HRID 2200125 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].[CH3:15][N:16]1[CH2:20][CH2:19][CH:18](O)[CH2:17]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:15][N:16]1[CH2:20][CH2:19][CH:18]([O:14][C:6]2[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:17]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 930741-Methyl-3-pyrrolidinolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27562513-Hydroxy-5-nitrobenzotrifluoride

Product 1

HCID 90032873HCID 90032873, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 3-nitro-5-(trifluoromethyl)phenol (1.6 g, 7.7 mmol), 1-methylpyrrolidin-3-ol (940 mg, 9.3 mmol), triphenylphosphine (3.4 g, 11.6 mmol) in THF (20 mL), stir on ice bath, then add diethyl azodicarboxylate (DEAD, 2.0 g, 11.6 mmol). Stir the mixture at ambient temperature for 15 hrs. Add water (100 mL), then extract the mixture with ethyl acetate (100 mL×3), combine the organic layers and dry over anhydrous sodium sulfate. Filter and concentrate the filtrate to get the crude product. Purify by flash chromatography (silica gel, DCM:MeOH=20:1) to afford the target product (1.5 g, 67%). MS: (M+1): 291.1.

Workup

  1. stirringStir the mixture at ambient temperature for 15 hrs
  2. extractionAdd water (100 mL), then extract the mixture with ethyl acetate (100 mL×3)
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationFilter
  5. concentrationconcentrate the filtrate
  6. customto get the crude product
  7. customPurify by flash chromatography (silica gel, DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-2e9b98d9a1a44149a82381df7502f231
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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