Triphenylphosphine → HCID 19707491, compound

HRID 726921Notes

Reaction equation

HRID 726921 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(P([N:65]=[N+:66]=[N-:67])(C2C=CC=CC=2)=O)C=CC=CC=1.C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C>[N:65]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)=[N+:66]=[N-:67]

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 5462977Diethyl azodicarboxylateHCID 19707473HCID 19707473, compound

Product 1

HCID 19707491HCID 19707491, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Step 1 (3.5 mmol) in 15 mL of THF at -0° C. was added triphenylphosphine (921 mg), followed by diethylazodicarboxylate (0.55 mL) and diphenylphosphoryl azide (0.75 mL). The solution was allowed to warm to room temperature overnight. After 48 hours, the reaction was poured into ethyl acetate and sat. aq. NaHCO3 solution, then washed with brine, dried (Na2SO4) and concentrated in vacuo to provide the crude product. Purification by chromatography on silica gel (50% CH2Cl2 /hexane) provided 360 mg of the titled compound.

Workup

  1. washwashed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto provide the crude product
  5. customPurification by chromatography on silica gel (50% CH2Cl2 /hexane)

Sources & evidence

ORD record
ord-91e9fa140332464bae0b7d41384d5b5f
Source dataset
uspto-grants-1998_01
Patent number
US05710171

Reaction notes

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