Water → HCID 53648298, compound

HRID 979174Notes

Reaction equation

HRID 979174 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C@@H:7]([CH:12]([CH3:14])[CH3:13])[C@H:6]([OH:15])[CH2:5]2.[H-].[Na+].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:21]=1.O>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C@@H:7]([CH:12]([CH3:13])[CH3:14])[C@H:6]([O:15][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:21]=1)[CH2:5]2

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 129263872-(Bromomethyl)-6-phenoxypyridineHCID 54053742HCID 54053742, compound

Product 1

HCID 53648298HCID 53648298, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of trans-5,6-dichloro-1-isopropyl-2-indanol (0.73 g), in anhydrous tetrahydrofuran (7 ml) was added to a suspension of sodium hydride (0.24 g, oil free) in anhydrous tetrahydrofuran (10 ml). The mixture was stirred for 40 minutes and a solution of 2-(bromomethyl)-6-phenoxypyridine (0.84 g) in anhydrous tetrahydrofuran was added, followed by a catalyst 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 combined ether extracts were dried (MgSO4) and condensed under reduced pressure to give an oil which was purified by flash chromatography to give trans-5,6-dichloro-1-isopropyl-2-((6-phenoxypyridin-2-yl)-methoxy)-indane (1.07 g).

Workup

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

Sources & evidence

ORD record
ord-081427a108bb425d89ab052179a6e01f
Source dataset
uspto-grants-1987_05
Patent number
US04666925

Reaction notes

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