Triphenylphosphine → HCID 67958379, compound

HRID 527667Notes

Reaction equation

HRID 527667 reaction equation
O[CH2:2][CH2:3][CH:4]([C:6]1[C:11]([O:12][CH2:13][O:14][CH3:15])=[CH:10][CH:9]=[CH:8][C:7]=1[OH:16])[CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH3:15][O:14][CH2:13][O:12][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:6]=1[CH:4]([CH3:5])[CH2:3][CH2:2][O:16]2

Participants

5

Reactant 3

HCID 11776Triphenylphosphine3×HCID 5363146Diisopropyl azodicarboxylate2×HCID 67958021HCID 67958021, compound

Product 1

HCID 67958379HCID 67958379, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 50 mL round-bottomed flask 2-(3-hydroxy-1-methyl-propyl)-3-(methoxymethoxy)phenol (56.3 mg, 0.249 mmol) was dissolved in Tetrahydrofuran (THF) to give a colourless solution. Triphenylphosphine (59.4 mg, 0.226 mmol) was added and the reaction mixture was stirred until complete solubilization of triphenylphosphine. DIAD (45.8 mg, 0.226 mmol) was added and the reaction mixture was stirred. Additional Triphenylphosphine (59.4 mg, 0.226 mmol) and DIAD (45.8 mg, 0.226 mmol) were added. The reaction mixture evaporated in vacuo and the residue was purified by flash chromatography (Biotage SP1) on silica gel using a 10 g SNAP silica cartridge as column and cyclohexane/ethyl acetate 10:1 as eluents affording the title compound (50.3 mg) as colorless oil.

Workup

  1. customto give a colourless solution
  2. customThe reaction mixture evaporated in vacuo
  3. customthe residue was purified by flash chromatography (Biotage SP1) on silica gel using a 10 g SNAP silica cartridge as column and cyclohexane/ethyl acetate 10:1 as eluents

Sources & evidence

ORD record
ord-0fb113f77f4b45f6a4f73872e1edff06
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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