Triphenylphosphine → HCID 89581116, compound

HRID 1501212Notes

Reaction equation

HRID 1501212 reaction equation
[OH:1][CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3].O[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)C)=O)=O)(C)C>O1CCCC1.O>[C:18]([C:17]1[CH:20]=[CH:21][C:22]([O:1][CH:2]([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[CH3:3])=[CH:15][CH:16]=1)#[N:19]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 133943-CyanophenolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 586417Methyl 4-(1-hydroxyethyl)benzoate

Product 1

HCID 89581116HCID 89581116, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(1-hydroxyethyl)benzoate (540 mg, 3 mmol), 3-hydroxybenzonitrile (360 mg, 3 mmol), triphenylphosphine (1.04 mg, 4 mmol), azodicarboxylic acid diisopropyl ester (800 mg, 4 mmol) in tetrahydrofuran (130 mL) were stirred at 20° C. for 12 hours. Water was added and the mixture was extracted with ethyl acetate (150 mL×3), the combined organic phase was dried by sodium sulfate, then filtered. The filtrate was evaporated in vacuum and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1) to give methyl 4-(1-(4-cyanophenoxy)ethyl)benzoate (370 mg, 45%) as colorless oil. LRMS (M+H+) m/z: calcd 281.11. found 281.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (150 mL×3)
  2. dry with materialthe combined organic phase was dried by sodium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuum
  5. customthe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-5a1b92b705364f50a4ecab3e4a744e99
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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