Triphenylphosphine → HCID 58245725, compound

HRID 1186044Notes

Reaction equation

HRID 1186044 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]#[N:12])[C:5](=[CH:8][C:9]=1[OH:10])[C:6]#[N:7].[CH2:13]([O:15][CH:16]([O:23][CH2:24][CH3:25])[CH2:17][CH:18]([CH2:21]O)[CH2:19]O)[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:24]([O:23][CH:16]([O:15][CH2:13][CH3:14])[CH2:17][CH:18]1[CH2:19][O:10][C:9]2[CH:8]=[C:5]([C:6]#[N:7])[C:4]([C:11]#[N:12])=[CH:3][C:2]=2[O:1][CH2:21]1)[CH3:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6433904,5-dihydroxyphthalonitrileHCID 122006482-(2,2-Diethoxyethyl)-1,3-propanediol

Product 1

HCID 58245725HCID 58245725, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To the mixture of 4,5-dihydroxy-phthalonitrile (2.50 g, 15.6 mmol), 2-(2,2-diethoxy-ethyl)-propane-1,3-diol (4.5 g, 23.4 mmol) and triphenylphosphine (6.138 g, 23.4 mmol) in THF (40 mL) was added diethyl azodicarboxylate (4.08 g, 23.4 mmol) and the resulting mixture heated at 75° C. overnight. The resulting mixture was then cooled to room temperature and evaporated in vacuo to yield a solid, which was purified via flash column chromatography (EA/Hex 2:3) to yield 3-(2,2-diethoxyethyl)-3,4-dihydro-2H-benzo[b][1,4]dioxepine-7,8-dicarbonitrile as a white solid. MS MH+=317, 1H NMR (CDCl3) δ 7.29 (s, 2H), 4.58 (m, 1H), 4.46 (m, 2H), 4.19 (m, 2H), 3.66 (m, 2H), 3.52 (m, 2H), 2.60 (m, 1H), 1.78 (m, 2H), 1.20 (t, J=7.0 Hz, 6H).

Workup

  1. temperatureThe resulting mixture was then cooled to room temperature
  2. customevaporated in vacuo
  3. customto yield a solid, which
  4. customwas purified via flash column chromatography (EA/Hex 2:3)

Sources & evidence

ORD record
ord-40a97a138e47490d8eeb1641c3a8d7f1
Source dataset
uspto-grants-2014_03
Patent number
US08673890B2

Reaction notes

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