Water → 1-{[4-(Difluoromethoxy)phenyl]ethynyl}-3-propylbenzene

HRID 30553

Reaction equation

HRID 30553 reaction equation
[F:1][CH:2]([F:31])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14](/[CH:18]=N/NS(C3C=CC(C)=CC=3)(=O)=O)[CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1.[CH2:32](B(CC)CC)[CH3:33].[OH-].[Na+].O>C1COCC1>[F:31][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:32][CH3:33])[CH:13]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7357TriethylboraneHCID 14798Sodium HydroxideHCID 59790336N-[(E)-[3-[2-[4-(difluoromethoxy)phenyl]ethynyl]phenyl]methylideneamino]-4-methylbenzenesulfonamide

Product 1

HCID 574358561-{[4-(Difluoromethoxy)phenyl]ethynyl}-3-propylbenzeneYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N′-[(1E)-(3-{[4-(difluoromethoxy)phenyl]ethynyl}phenyl)methylene]-4-methylbenzenesulfonohydrazide (0.67 mg, 1.52 mmol) in THF was treated with triethyl borane (1.0 M in THF, 1.52 mL, 1.52 mmol), stirred for 2 minutes, treated with NaOH (2.5 N, 0.61 mL, 1.52 mmol), refluxed for 2 hours, cooled to room temperature, poured into water and extracted with EtOAc. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo. The resultant residue was purified on silica gel (ISCO) using hexanes/EtOAc (50/1) as the eluting solvents to give 1-{[4-(difluoromethoxy)phenyl]ethynyl}-3-propylbenzene as a clear oil (386 mg, 89% yield), MS m/e (M+H)+ 286; 1H NMR (400 MHz, DMSO-d6) 0.85 (t, J=7.32 Hz, 3H), 1.57 (m, 2H), 2.6 (t, J=7.32 Hz, 2H), 7.2 (m, 3H), 7.35-7.45 (m, 4H), 7.58 (d, J=8.79 Hz, 2H).

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified on silica gel (ISCO)

Sources & evidence

ORD record
ord-2afa4f797d6842c69a7d8f1808c9d185
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Linked notes

Loading…