Triphenylphosphine → HCID 9823905, compound

HRID 275968Notes

Reaction equation

HRID 275968 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[C:43](=[CH: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][CH:45]=[C: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 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 234458302-(9H-Fluoren-9-ylidene)ethan-1-ol

Product 1

HCID 9823905HCID 9823905, compound

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-fluoren-9-ylidene-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 72 h. The resulting mixture was treated with water (50 ml), and the products extracted into dichloromethane (3×20 ml). The extracts were combined, washed with brine, dried (Na2SO4) and evaporated to a yellow gum. This was then purified by column chromatography on silica gel (15% Et2O in petroleum eluent) to give ethyl 2-ethoxy-3-[4-(2-fluoren-9-ylidene-ethoxy)-phenyl]-propionate as a yellow gum; 0.28 g (60%).

Workup

  1. stirringstirring
  2. waitcontinued for 72 h
  3. extractionthe products extracted into dichloromethane (3×20 ml)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to a yellow gum
  7. customThis was then purified by column chromatography on silica gel (15% Et2O in petroleum eluent)

Sources & evidence

ORD record
ord-99aeab48e28b49fe8a60fe25ed205e02
Source dataset
uspto-grants-2002_03
Patent number
US06353018B1

Reaction notes

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