Allyl bromide → HCID 18464852, compound

HRID 323303Notes

Reaction equation

HRID 323303 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH:11]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12]#[N:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O1C[CH2:24][CH2:23][CH2:22]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(Br)C=C>C(OCC)(=O)C.CCCCCC.O.CN(C)P(N(C)C)(N(C)C)=O>[Si:1]([O:8][CH2:9][CH2:10][C:11]([CH2:24][CH:23]=[CH2:22])([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:12]#[N:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 184645022-(2-(t-Butyldimethylsilyloxy)ethyl)-3-phenylpropionitrile

Product 1

HCID 18464852HCID 18464852, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Combine 2-(2-(t-butyldimethylsilyloxy)ethyl)-3-phenylpropionitrile (1.32 g,4.55 mmol) and tetrahydrofuran (8 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of lithium bis(trimethylsilyl)amide (9.1 mL, 1 M in THF, 9.1 mmol). After 30 minutes, add hexamethylphosphoramide (0.25 mL) and allyl bromide (1.10 g, 9.1 mmol). Warm slowly to ambient temperature. After 12 hours, add water and separate the layers. Extract the aqueous layer three times with ethyl acetate. Combine the organic layers and extract with aqueous 1 M hydrochloric acid solution. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 5% ethyl acetate/hexane to give the title compound: Rf=0.83 (silica gel, 1/4 ethyl acetate/hexane).

Workup

  1. temperatureWarm slowly to ambient temperature
  2. waitAfter 12 hours
  3. customseparate the layers
  4. extractionExtract the aqueous layer three times with ethyl acetate
  5. extractionextract with aqueous 1 M hydrochloric acid solution
  6. dry with materialDry the combined organic layers over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customto obtain a residue

Sources & evidence

ORD record
ord-e021e76fc36f4edb9f32329fb406b18e
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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