Water → HCID 13853681, compound

HRID 979172Notes

Reaction equation

HRID 979172 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@@H:7]([CH:11]([CH3:13])[CH3:12])[C@H:6]([OH:14])[CH2:5]2.[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:20]=1.O>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@@H:7]([CH:11]([CH3:12])[CH3:13])[C@H:6]([O:14][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:20]=1)[CH2:5]2

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 129263872-(Bromomethyl)-6-phenoxypyridineHCID 53882928HCID 53882928, compound

Product 1

HCID 13853681HCID 13853681, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of trans-5-chloro-1-isopropyl-2-indanol (0.75 g) in anhydrous tetrahydrofuran (5 ml) was added to a suspension of sodium hydride (0.28 g, oil free) in anhydrous tetrahydrofuran (5 ml). The mixture was stirred for 0.5 hr and 2-(bromomethyl)-6-phenoxypyridine (1 g) in anhydrous tetrahydrofuran (5 ml) was added, followed by a catalytic amount of tetra-n-butylammonium iodide. The mixture was stirred at room temperature for 18 hours, mixed with water (100 ml) and extracted with diethyl ether (3×50 ml). The ether extract was dried (MgSO4) and condensed under reduced pressure to give an oil that was purified by flash chromatography to give trans-5-chloro-1-isopropyl-2-((6-phenoxypyridin-2-yl)-methoxy)indane (0.94 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionextracted with diethyl ether (3×50 ml)
  3. extractionThe ether extract
  4. customwas dried
  5. custom(MgSO4) and condensed under reduced pressure
  6. customto give an oil that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-b44754abac10407a8a5fe81dc6c232ab
Source dataset
uspto-grants-1987_05
Patent number
US04666925

Reaction notes

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