Triphenylphosphine → HCID 11730000, compound

HRID 275977Notes

Reaction equation

HRID 275977 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([O:27][CH2:28][CH3:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:49]1[C:62]2[CH:61]([CH2:63][CH2:64]O)[C:60]3[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=3)[O:54][C:53]=2[CH:52]=[CH:51][CH:50]=1>C1COCC1>[CH2:28]([O:27][CH:21]([CH2:20][C:17]1[CH:16]=[CH:15][C:14]([O:13][CH2:64][CH2:63][CH:61]2[C:62]3[CH:49]=[CH:50][CH:51]=[CH:52][C:53]=3[O:54][C:55]3[C:60]2=[CH:59][CH:58]=[CH:57][CH:56]=3)=[CH:19][CH:18]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:29]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 23445773HCID 23445773, compound

Product 1

HCID 11730000HCID 11730000, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl azodicarboxylate (40% solution in toluene, 1.61 g, 9.3 mmol) was added dropwise, under argon, over 10 min to a solution of ethyl 3-(4-hydroxyphenyl)-2-ethoxypropionate (2.23 g, 9.3 mmol) and triphenylphosphine (2.43 g, 9.3 mmol) in THF (45 ml). The mixture was stirred for 15 min, then a solution of 2-(9H-xanthen-9-yl)ethanol (2.0 g, 9.3 mmol) in THF (10 ml) was added dropwise over 10 min. The resulting mixture was stirred at room temperature for 60 h. The solvent was evaporated, the residue stirred with benzene (20 ml) and the resulting crystalline solid filtered off. The filtrate was evaporated and the residue purified by column chromatography on silica gel (benzene eluent) to give the title compound as an oil: (1.9 g, 45.8%).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 60 h
  2. customThe solvent was evaporated
  3. stirringthe residue stirred with benzene (20 ml)
  4. filtrationthe resulting crystalline solid filtered off
  5. customThe filtrate was evaporated
  6. customthe residue purified by column chromatography on silica gel (benzene eluent)

Sources & evidence

ORD record
ord-0fb29c3fa5074d1ba8bc7b3659c8a789
Source dataset
uspto-grants-2002_03
Patent number
US06353018B1

Reaction notes

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