Triphenylphosphine → HCID 178473588, compound

HRID 868001Notes

Reaction equation

HRID 868001 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][CH2:21][O:22][C:23](/[N:25]=[N:26]/[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:24]>C1COCC1>[CH3:31][CH2:30][O:29][C:27](/[N:26]=[N:25]/[C:23]([O:22][CH2:21][CH3:20])=[O:24])=[O:28].[C:14]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylate2×

Product 1

HCID 178473588HCID 178473588, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of D-2 (304 mg) and triphenylphosphine (524 mg) in dry THF (5 ml) is stirred at room temperature under argon and DEAD (0.32 ml, 4 mmole) is added via syringe. The solution warms upon addition of DEAD and is allowed to cool to 20°-25° over a period of 30 min. The reaction mixture is concentrated in vacuo, and the residue chromatographed on silica gel (elution with ethyl acetate/hexane, 1:2) to deliver D-3 as a solid, m.p. 96.5-97.5° (hexane/diethyl ether): [α]D25 -76.2° (c 0.795, MeOH); IR (cm-1, mull) 3348, 2951, 1797, 1792, 1682, 1537, 1250, 1176; PMR (80 MHz, CDCl3 δ) 4.55-4.17, 4.17-3.60, 3.78, 2.60, 2.56, 1.88-1.09, 1.43, 0.94; MS (Cl, NH3, m/z) 248, 304, 204, 266, 305.

Workup

  1. temperatureto cool to 20°-25° over a period of 30 min
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customthe residue chromatographed on silica gel (elution with ethyl acetate/hexane, 1:2)

Sources & evidence

ORD record
ord-979dea2e4ca1462ebabfb18e54d081c6
Source dataset
uspto-grants-1988_10
Patent number
US04777286

Reaction notes

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