Triphenylphosphine → ethyl 2-ethoxy-3-[4-(2-(9H-fluoren-9-yl)ethoxy]phenyl)propionate

HRID 275972Notes

Reaction equation

HRID 275972 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:32]1[C:44]2[CH:43]([CH2:45][CH2:46][OH:47])[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:36]=2[CH:35]=[CH:34][CH:33]=1.[CH2:48]([O:50][CH:51]([CH2:57][C:58]1[CH:63]=[CH:62][C:61](O)=[CH:60][CH:59]=1)[C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH3:49]>C1COCC1.O>[CH2:48]([O:50][CH:51]([CH2:57][C:58]1[CH:59]=[CH:60][C:61]([O:47][CH2:46][CH2:45][CH:43]2[C:44]3[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=3[C:37]3[C:42]2=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:62][CH:63]=1)[C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH3:49]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10921761Fluorene-9-ethanolHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 9824017ethyl 2-ethoxy-3-[4-(2-(9H-fluoren-9-yl)ethoxy]phenyl)propionate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl azodicarboxylate (0.235 ml, 1.49 mmol) was added at 0° C. to a stirred solution of triphenylphosphine (0.392 g, 1.49 mmol) and 2-(9H-fluoren-9-yl)-ethanol (0.208 g, 1.0 mmol) in dry THF (5 ml) and the mixture stirred for 5 min. A solution of ethyl 2-ethoxy-3-(4-hydroxy-phenyl)-propionate (0.356 g, 1.49 mmol) in dry THF (5 ml) was then added, the mixture allowed to warm to room temperature and stirring continued for 20 h. The resulting mixture was treated with water (50 ml), and the products extracted into dichloromethane (4×50 ml). The extracts were combined, washed with brine, dried (Na2SO4) and evaporated to a colourless gum. This was then purified by column chromatography on SiO2 (15% Et2O in petroleum eluent) to give the title compound as a colourless gum; 0.20 g (47%).

Workup

  1. stirringstirring
  2. waitcontinued for 20 h
  3. extractionthe products extracted into dichloromethane (4×50 ml)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to a colourless gum
  7. customThis was then purified by column chromatography on SiO2 (15% Et2O in petroleum eluent)

Sources & evidence

ORD record
ord-e5f7435b1281465e9a4aed7cef57f657
Source dataset
uspto-grants-2002_03
Patent number
US06353018B1

Reaction notes

Loading…