Triphenylphosphine → HCID 135474625, compound

HRID 1816408Notes

Reaction equation

HRID 1816408 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[N:10][OH:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[C:3]3[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=3[O:11][N:10]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 136342143HCID 136342143, compound

Product 1

HCID 135474625HCID 135474625, compoundYield 4.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2,5-dihydroxyphenyl)(4-hydroxyphenyl)methanone (1.0 g, 4.3 mmol), hydroxylamine hydrochloride (2.0 g, 29 mmol), pyridine (5 mL) and EtOH (30 mL) was heated to reflux. After stirring for 4 h, the reaction was cooled, poured into 2N HCl and extracted with EtOAc. The organic layer was dried over MgSO4, and concentrated to give a yellow foam (0.92 g, 87% yield). The product, (2,5-dihydroxyphenyl)(4-hydroxyphenyl)methanone oxime (0.9 g, 3.7 mmol) was taken in THF (25 mL) and triphenylphosphine (1.5 g, 5.6 mmol) first was added, followed by the dropwise addition of diethylazodicarboxylate (0.9 mL, 5.6 mmol). After 30 min the reaction was filtered, concentrated and the resulting oil was purified by column chromatography (eluent 30% EtOAc/hexanes) to give a solid. The solid was triturated with CH2Cl2, and filtered to give a solid (0.04 g, m.p. 266-268° C.); 1H NMR (DMSO-d6) 10.32 (s, 1H), 10.30 (s, 1H), 8.00 (d, 2H, J=8.7 Hz), 7.50 (d, 1H, J=8.7 Hz), 7.02 (d, 1H, J=2.3 Hz), 6.95 (d, 2H, J=8.7 Hz), 6.93 (dd, 1H, J=8.7 Hz, 2.4 Hz); MS m/e 228 (M+H)+.

Workup

  1. filtrationAfter 30 min the reaction was filtered
  2. concentrationconcentrated
  3. customthe resulting oil was purified by column chromatography (eluent 30% EtOAc/hexanes)
  4. customto give a solid
  5. customThe solid was triturated with CH2Cl2
  6. filtrationfiltered

Sources & evidence

ORD record
ord-8943e7dc7cf74691aa8b98388d08731a
Source dataset
uspto-grants-2005_04
Patent number
US06884814B2

Reaction notes

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