Triphenylphosphine → HCID 18782614, compound

HRID 1420811Notes

Reaction equation

HRID 1420811 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Br:32][C:33]1[CH:38]=[C:37]([O:39][C:40]([F:43])([F:42])[F:41])[CH:36]=[C:35]([CH2:44][CH2:45]O)[C:34]=1[OH:47]>O1CCCC1>[Br:32][C:33]1[C:34]2[O:47][CH2:45][CH2:44][C:35]=2[CH:36]=[C:37]([O:39][C:40]([F:41])([F:42])[F:43])[CH:38]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 18782666HCID 18782666, compound

Product 1

HCID 18782614HCID 18782614, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) of triphenylphosphine (6.11 g, 0.0234 mol) in tetrahydrofuran (40 ml) was added diethylazodicarboxylate (3.7 ml, 0.0234 mol). The solution was stirred for 30 min., whereupon a solution of 2-bromo-6-(2-hydroxyethyl)-4-trifluoromethoxyphenol (Desc 16.; 5.4 g, 0.018 mol) in tetrahydrofuran was added. The solution was stirred at room temperature for 15 h. and then the solvent was removed in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with water, saturated brine, dried (MgSO4). After removal of the solvent in vacuo the residue was purified by chromatography on silica gel (eluting with 10% ethyl acetate in hexane) to give the title compound as a pink oil. 1H NMR (250 MHz, CDCl3) δ2.93 (2H, t, J 5.6 Hz), 3.98 (2H, t, J 5.4 Hz), 6.96 (1H, d, J 2.5 Hz), and 7.30 (1H, d, J 2.4 Hz).

Workup

  1. additionwas added
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with water, saturated brine
  5. dry with materialdried (MgSO4)
  6. customAfter removal of the solvent in vacuo the residue
  7. customwas purified by chromatography on silica gel (eluting with 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6df076faf40b46568368f01fc85ad2c6
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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