Triphenylphosphine → 5-[4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenyloxy]pent-2-yl acetate

HRID 1919770Notes

Reaction equation

HRID 1919770 reaction equation
[C:1]([O:4][CH:5]([CH2:7][CH2:8][CH2:9][OH:10])[CH3:6])(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC([O-])=O.[F:40][C:41]([F:62])([F:61])[C:42]([C:51]1[CH:56]=[CH:55][C:54](O)=[C:53]([CH2:58][CH2:59][CH3:60])[CH:52]=1)([O:47][CH2:48][O:49][CH3:50])[C:43]([F:46])([F:45])[F:44]>O1CCCC1>[C:1]([O:4][CH:5]([CH2:7][CH2:8][CH2:9][O:10][C:54]1[CH:55]=[CH:56][C:51]([C:42]([O:47][CH2:48][O:49][CH3:50])([C:43]([F:46])([F:45])[F:44])[C:41]([F:40])([F:61])[F:62])=[CH:52][C:53]=1[CH2:58][CH2:59][CH3:60])[CH3:6])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 151289525-Hydroxypent-2-yl acetateHCID 592010374-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenolHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 592351335-[4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenyloxy]pent-2-yl acetateYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Hydroxypent-2-yl acetate (58.5 mg), triphenylphosphine (131 mg) and ethyl azodicarboxylate (2.2 mol/L, 200 μL) were added to a mixed solution of 4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenol (69.3 mg, 200 μmol) in tetrahydrofuran (2 mL) at room temperature. After completion of the reaction, the solvent was evaporated, and the residue was purified by silica gel preparative thin-layer chromatography (hexane:ethyl acetate=5:1) to obtain 80.4 mg of the title compound (yield: 85%) as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe residue was purified by silica gel preparative thin-layer chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-1c70ace4880e4db0b928ab9eb0ef2bac
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

Loading…