Triphenylphosphine → Diphenyl Ether

HRID 1279925Notes

Reaction equation

HRID 1279925 reaction equation
C([C:5]1[CH:6]=[C:7](C2OC=C(CCO)N=2)[CH:8]=[C:9](C(C)(C)C)[C:10]=1[OH:11])(C)(C)C.C(NCC[C:31]1[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=1)(=O)CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:31]1([O:11][C:10]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 14717710N-[2-(4-Hydroxyphenyl)ethyl]propanamideHCID 135509425HCID 135509425, compound

Product 1

HCID 7583Diphenyl EtherYield 109.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(3,5-di-t-butyl-4-hydroxyphenyl)-4-(2-hydroxyethyl)oxazole (5.51 g, 17.38 mmole) in tetrahydrofuran (47 ml) was added N-ethyl, N-propionyl tyramine (3.5 g, 15.8 mmole) and triphenylphosphine (4.55 g, 17.38 mmole). After cooling to 0° C., a solution of diethylazodicarboxylate (2.73 ml, 17.38 mmole) in tetrahydrofuran (16 ml) was added dropwise over 10 minutes. The reaction was allowed to warm to room temperature and stir for 22 hours, evaporated, and triturated with methylene chloride (50 ml) and filtered. The filtrate was chromatographed on silica gel twice using methylene chloride-ethyl acetate and hexane-acetone gradients to give the intermediate phenyl ether (2.95 g, 36%):

Workup

  1. temperatureto warm to room temperature
  2. customevaporated
  3. customtriturated with methylene chloride (50 ml)
  4. filtrationfiltered
  5. customThe filtrate was chromatographed on silica gel twice using methylene chloride-ethyl acetate and hexane-acetone gradients

Sources & evidence

ORD record
ord-06eb8281c0db40fc8f02423e53dcf2fb
Source dataset
uspto-grants-2002_09
Patent number
US06448396B2

Reaction notes

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