Triphenylphosphine → HCID 68535529, compound

HRID 644226Notes

Reaction equation

HRID 644226 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][N:33]1[CH2:38][CH2:37][CH:36](O)[CH2:35][CH2:34]1.N(C(OCC)=O)=NC(OCC)=O>CO.C1C=CC=CC=1>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH:36]2[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]2)[CH:3]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 660484-Piperidinol, 1-methyl-HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2775386Methyl 4-fluorosalicylate

Product 1

HCID 68535529HCID 68535529, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of methyl 4-fluoro-2-hydroxybenzoate (12 g, 70.5 mmol), triphenyl-phosphine (22.2 g, 84.6 mmol), N-methyl-4-hydroxypiperidine (8.1 g, 70.3 mmol) and benzene (25 mL) was heated until all the solids dissolved. The solution was cooled to 0° C., then sonicated while adding diethyl azodicarboxylate (14.7 g, 84.6 mmol) dropwise. After the addition was complete, the reaction was sonicated for an additional 60 minutes, and then purified by flash chromatography, eluting sequentially with 50% EtOAc in hexanes followed by 1%, 2%, 5% then 10% MeOH in CHCl3, to yield 10.8 g (40.4 mmol, 57%) of an oil.

Workup

  1. temperaturewas heated until all the solids
  2. dissolutiondissolved
  3. customsonicated
  4. additionAfter the addition
  5. customthe reaction was sonicated for an additional 60 minutes
  6. custompurified by flash chromatography
  7. washeluting sequentially with 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-40faa98fb7e2400e98221da367626b27
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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