Triphenylphosphine → HCID 58045746, compound

HRID 657979Notes

Reaction equation

HRID 657979 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]([F:21])([F:20])[CH2:17][CH2:18]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC1C=CC(Cl)=CC=1)=O)=NC(OCC1C=CC(Cl)=CC=1)=O>ClCCl>[C:1]([C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[C:9]([O:11][CH2:18][CH2:17][C:16]([F:21])([F:20])[F:15])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1375123,3,3-Trifluoro-1-propanolHCID 51979911Di-(4-chlorobenzyl)azodicarboxylateHCID 58045815HCID 58045815, compound

Product 1

HCID 58045746HCID 58045746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(3-tert-butyl-5-hydroxyphenyl)ethanone (O3.106; 300 mg, 1.56 mmol), 3,3,3-trifluoropropanol (178 mg, 1.56 mmol) and triphenylphosphine (409 mg, 1.56 mmol) in dichloromethane (5 ml) at RT was added a solution of di(4-chlorobenzyl) azodicarboxylate (573 mg, 1.56 mmol) in dichloromethane (1 ml). The mixture was stirred for 5 days and then filtered. The solvent was removed and the residue was purified by flash chromatography (n-heptane:ethyl acetate). Yield: 170 mg, 38%.

Workup

  1. filtrationfiltered
  2. customThe solvent was removed
  3. customthe residue was purified by flash chromatography (n-heptane:ethyl acetate)

Sources & evidence

ORD record
ord-728395a0ee21453eb32eec4b434435e5
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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