1,3-Dioxolane, 2-(phenylmethyl)- → HCID 19082234, compound

HRID 265298Notes

Reaction equation

HRID 265298 reaction equation
[C:1]1([CH2:7][CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][C:16]#[N:17].[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[C:1]1([CH2:7][CH2:8][O:12][CH2:11][CH2:10][O:9][CH2:14][CH2:15][C:16]#[N:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 75621,3-Dioxolane, 2-(phenylmethyl)-HCID 14798Sodium HydroxideHCID 170203-Bromopropionitrile

Product 1

HCID 19082234HCID 19082234, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(2-phenylethoxy)ethanol (8.0 g, prepared from 2-phenylmethyl 1,3-dioxolane according to the general method in Can. J. Chem., 1974, 52, 888), 3-bromopropanenitrile (5.6 ml), sodium hydroxide (50 g) and tetrabutylammonium chloride (0.5 g) in dichloromethane (100 ml) and water (100 ml) was stirred at room temperature for 72 hours. The mixture was diluted with water and the organic layer separated. The aqueous layer was extracted with a further portion of dichloromethane. The combined organic extracts were washed with dilute aqueous hydrochloric acid and water, dried (MgSO4) and evaporated under reduced pressure to yield the crude product. This material was purified by flash chromatography over silica using 1:1 ether:petroleum ether (bp 60°-80°) as eluant to give the subtitled compound as an oil (9.84 g, 90% ).

Workup

  1. customthe organic layer separated
  2. extractionThe aqueous layer was extracted with a further portion of dichloromethane
  3. washThe combined organic extracts were washed with dilute aqueous hydrochloric acid and water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto yield the crude product
  7. customThis material was purified by flash chromatography over silica using 1:1 ether

Sources & evidence

ORD record
ord-00d7d368ac524d61bd2219f2643035b6
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Reaction notes

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