Triphenylphosphine → HCID 86760859, compound

HRID 2112736Notes

Reaction equation

HRID 2112736 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][OH:5].O[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([NH2:16])=[O:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([NH2:16])=[O:15]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 70964(2-Hydroxyphenyl)ureaHCID 5462977Diethyl azodicarboxylateHCID 6973630(-)-Glycidol

Product 1

HCID 86760859HCID 86760859, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (2S)-oxiran-2-ylmethanol (296 mg, 4.0 mmol), N-(2-hydroxyphenyl)urea (609 mg, 4.0 mmol) and triphenylphosphine (1.05 g, 4.0 mmol) in THF (10 mL) was dropwise added DEAD (697 mg, 4.0 mmol) in THF (3 mL) at room temperature. After addition was completed the reaction mixture was stirred at room temperature over night. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (0-80% ethyl acetate in petroleum spirit) to give sub-title compound (336 mg).

Workup

  1. customat room temperature
  2. additionAfter addition
  3. customThe volatiles were removed in vacuo
  4. customthe residue was purified by silica gel flash chromatography (0-80% ethyl acetate in petroleum spirit)

Sources & evidence

ORD record
ord-b89229e139f74cc3a3f58b25fa85fc0e
Source dataset
uspto-grants-2009_04
Patent number
US07524856B2

Reaction notes

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