Triphenylphosphine → HCID 12401049, compound

HRID 1369288Notes

Reaction equation

HRID 1369288 reaction equation
O[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH:11]1[C:6]2[S:5][CH2:4][CH2:3][CH2:2][O:12][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18519030HCID 18519030, compound

Product 1

HCID 12401049HCID 12401049, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To 2-(3-hydroxy-propylsulfanyl)-phenol (29.2 g, 158.5 mmol) in THF (450 mL) was added triphenylphosphine (52.0 g, 200.0 mmol). The solution was cooled to −40° C. and diethyl azodicarboxylate (31.5 mL, 164.0 mmol) was added slowly. The solution was warmed to rt and stirred for 2.5 h. The THF was removed by evaporation and the residue was treated with 1 L of Et2O. The formed solids were filtered off, and the filtrate concentrated to an oil which was purified over silica gel (10% Et2O/hexane) to a pink oil (16.2 g, 61%).

Workup

  1. temperatureThe solution was warmed to rt
  2. customThe THF was removed by evaporation
  3. additionthe residue was treated with 1 L of Et2O
  4. filtrationThe formed solids were filtered off
  5. concentrationthe filtrate concentrated to an oil which
  6. customwas purified over silica gel (10% Et2O/hexane) to a pink oil (16.2 g, 61%)

Sources & evidence

ORD record
ord-dd264cd17c424f878120310db6af2635
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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