Tetrahydrofuran → HCID 57612782, compound

HRID 1668409Notes

Reaction equation

HRID 1668409 reaction equation
[CH2:1]1[O:6][C:4](=[O:5])[NH:3][CH:2]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li]CCCC.[Br:19]CCCCC(Cl)=O.[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1>>[CH2:7]([C@H:2]1[CH2:1][O:6][C:4](=[O:5])[N:3]1[C:29](=[O:30])[CH2:28][CH2:27][CH2:31][Br:19])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 5211735-Bromovaleryl chlorideHCID 5596684-Benzyl-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 57612782HCID 57612782, compoundYield 99.7%

Conditions

Temperature
-70 °C

Procedure

To a solution of S-(−)-4-benzyl-2-oxazolidinone (8.0 g, 45.1 mmol) in THF (75 mL) at −70° C., is added n-BuLi (19.8 mL, 49.6 mmol, 2.5 M in hexane) slowly. After stirring at −70° C. for 1 hour, 5-bromovaleryl chloride (11.7 g, 58.7 mmol) is added dropwise. After stirring at −70° C. for 20 minutes, the cooling bath is removed and the reaction mixture is warmed to 25° C. and stirred for 2 hours. The solution is diluted with 150 mL of ether, and washed with 2×100 mL of water. The combined organic layers is dried over Na2SO4 and concentrated. The crude product is purified by chromatography (hexane/EtOAc:85/15) to give a white solid (15.3 g, 99.7%). (NMR and MS data confirmed, U-3133-51-24).

Workup

  1. stirringAfter stirring at −70° C. for 20 minutes
  2. customthe cooling bath is removed
  3. temperaturethe reaction mixture is warmed to 25° C.
  4. stirringstirred for 2 hours
  5. additionThe solution is diluted with 150 mL of ether
  6. washwashed with 2×100 mL of water
  7. dry with materialThe combined organic layers is dried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product is purified by chromatography (hexane/EtOAc:85/15)

Sources & evidence

ORD record
ord-e5e35b7802a24e7091b22f2f34bfd66f
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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