Triphenylphosphine → HCID 178426037, compound

HRID 2404155Notes

Reaction equation

HRID 2404155 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:16])[CH:8]=2)[N:3]=1.[C:17]([C@@H:21]1[CH2:26][CH2:25][C@H:24](O)[CH2:23][CH2:22]1)([CH3:20])([CH3:19])[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1.C1COCC1>[C:17]([C@H:21]1[CH2:26][CH2:25][C@H:24]([O:16][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([CH3:1])[CH:11]=[C:10]3[C:12]([F:13])([F:15])[F:14])[CH2:23][CH2:22]1)([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 669259052-Methyl-4-trifluoromethyl-quinolin-6-olHCID 178445811HCID 178445811, compound

Product 1

HCID 178426037HCID 178426037, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-4-trifluoromethyl-quinolin-6-ol (0.771 g, 0.00339 mol, cis-4-tert-Butyl-cyclohexanol (0.8570 g, 0.005484 mol) and Triphenylphosphine (1.423 g, 0.005425 mol) were placed in a flask, and dissolved in Toluene (25 mL). For the Mitsunobu reaction of certain analogs, THF was substituted for toluene as solvent. Diisopropyl azodicarboxylate (1.137 mL, 0.005430 mol) was then added dropwise. After 3 d stirring at RT, the reaction was evaporated to dryness. The residue was purified by silica gel chromatography using 0-30% ethyl acetate in hexanes as eluent (Rf=0.38 in 3:1 hexanes/ethyl acetate). Isolated was 0.739 g of product (60%). ESI-MS (M+H+): 366.20.

Workup

  1. customthe reaction was evaporated to dryness
  2. customThe residue was purified by silica gel chromatography
  3. customIsolated

Sources & evidence

ORD record
ord-396f03af37914a7aaf702119fda81424
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

Loading…