4-Chlorophenol → HCID 69424971, compound

HRID 459261Notes

Reaction equation

HRID 459261 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:32][O:33][C:34](=[O:52])[C:35]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[CH:40][CH:39]=1)([OH:37])[CH3:36].[Cl:53][C:54]1[CH:59]=[CH:58][C:57](O)=[CH:56][CH:55]=1>C1COCC1>[CH3:32][O:33][C:34](=[O:52])[C:35]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[CH:40][CH:39]=1)([O:37][C:57]1[CH:58]=[CH:59][C:54]([Cl:53])=[CH:55][CH:56]=1)[CH3:36]

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 62214478HCID 62214478, compound

Product 1

HCID 69424971HCID 69424971, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of triphenylphosphin(0.1 g, 0.38 mmol) in 5 ml of dry THF was treated at 0° C. with DEAD (0.066 g, 0.38 mmol) and stirred over 30 min. Then a solution of 4-Benzyloxyphenyl-2-hydroxypropanoic acid methyl ester (0.1 g, 0.35 mmol) and p-chlorophenol (0.048 g, 0.38 mmol) in 2 ml of THF was added to the solution and the mixture reaction was stirred at room temperature overnight. The mixture was concentrated to dryness and chromatographed in silicagel (hexanes/Ethyl acetate 3:1) to give 0.082 g of product (60%). 1H-NMR (200.15 MHz, CDCl3): δ 7.46–7.31 (m, 5H), 7.28–7.13 (m, 4H), 6.93 (d, 2H, J=8.8), 6.75 (d, 2H, J=8.8), 5.04 (s, 2H), 4.73(t, 1H, J=6.1), 3.71 s (s, 3H), 3.18 (d, 2H, J=6.4).

Workup

  1. customthe mixture reaction
  2. stirringwas stirred at room temperature overnight
  3. concentrationThe mixture was concentrated to dryness
  4. customchromatographed in silicagel (hexanes/Ethyl acetate 3:1)

Sources & evidence

ORD record
ord-dee836da3baa4d0199a498ec66450d9d
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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