1,2-Dibromoethane → HCID 18630141, compound

HRID 376687Notes

Reaction equation

HRID 376687 reaction equation
Cl[C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Si:20]([CH3:23])([CH3:22])[CH3:21])[C:3]=1[C:4]([N:6]([CH2:14][CH3:15])[CH:7]([O:12][CH3:13])[C:8]([CH3:11])([CH3:10])[CH3:9])=[O:5].[CH3:24][N:25](CCN(C)C)[CH3:26].[Li]C(C)(C)C.CCCCC.BrCCBr>C1COCC1.C([O-])(O)=O.[Na+]>[CH3:24][N:25]([CH3:26])[C:19]1[CH:18]=[CH:17][C:16]([Si:20]([CH3:23])([CH3:22])[CH3:21])=[C:3]([CH:2]=1)[C:4]([N:6]([CH2:14][CH3:15])[CH:7]([O:12][CH3:13])[C:8]([CH3:11])([CH3:10])[CH3:9])=[O:5]

Participants

8

Reactant 5

HCID 78391,2-DibromoethaneHCID 8003PentaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 10713229HCID 10713229, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 18630141HCID 18630141, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of the compound of Example 201 (0.72 g, 2.0 mmol) and TMEDA (1.20 mL, 8.0 mmol) in THF (30 mL) at -78° C. was treated with a solution of 1.7 M t-BuLi in pentane (5.6 mL, 9.6 mmol) and allowed to slowly warm to -20° C. over 4 h. The reaction was quenched with 1,2-dibromoethane (0.86 mL, 10 mmol), was diluted with sat NaHCO3, extracted with ether, the organic layers washed with brine, dried (MgSO4) and concentrated to afford the title compound. The crude product was purified by RC (ethyl acetate/hexanes) and recrystallization from pentane (-78° C.) to afford the title compound as a white solid (0.14 g, 20%). m.p. 96°-98° C.

Workup

  1. extractionextracted with ether
  2. washthe organic layers washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f252b0e897c3402bb2fdc82dfbb14746
Source dataset
uspto-grants-2000_02
Patent number
USRE036562

Reaction notes

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