Triphenylphosphine → HCID 178426037, compound

HRID 713935Notes

Reaction equation

HRID 713935 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-04afca80d4ad44babe1676d8241c98a3
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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