N,N,N',N'-Tetramethylethylenediamine → HCID 59791330, compound

HRID 402219Notes

Reaction equation

HRID 402219 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CN(CCN(C)C)C.[Li]CCCC.[Cl:28][CH2:29][CH2:30][CH2:31]I>C1COCC1.CCCCCCC.CCOC(C)=O>[Cl:28][CH2:29][CH2:30][CH2:31][C:12]1[O:11][C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 813631-Chloro-3-iodopropaneHCID 10976930tert-Butyl[(furan-2-yl)methoxy]dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 59791330HCID 59791330, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(t-butyldimethylsilyloxymethyl)furan (5 g, 0.023 mol) in THF (48 mL) was dried over 3 {acute over (Å)} molecular sieves. After the sieves were removed, an additional 10 mL THF was added along with TMEDA (3.47 mL, 0.023 mol), and the solution was cooled to 0° C. in an ice bath. A solution of BuLi (10.1 mL of 2.5M in hexane, 0.025 mol) was added dropwise over 25 minutes. The mixture was allowed to stir for 1 hour. 1-chloro-3-iodopropane (5.64 g, 0.028 mol) was injected rapidly. After 2 hours TLC indicated completion. The solvent was evaporated, and the material was partitioned between ether (100 mL) and 5% citric acid (100 mL). The ether layer was washed with water (50 mL) and then brine (50 mL). The ether solution was dried with sodium sulfate, filtered, and evaporated. The resulting material was flashed on silica using 20/1 heptane/EtOAc. Appropriate fraction were combined and evaporated to yield 4.9 g (75% yield). TLC: Rf 0.6 (Heptane/EtOAc 5/1) 1H NMR: (CDCl3) δ 0.00 (s, 6H), 0.83 (s, 9H), 2.01 (p, 2H), 2.71 (t, 2H), 3.48 (t, 2H), 4.51 (s, 2H), 5.88 (d, 1H), 6.04 (d, 1H)

Workup

  1. customAfter the sieves were removed
  2. waitAfter 2 hours TLC indicated completion
  3. customThe solvent was evaporated
  4. customthe material was partitioned between ether (100 mL) and 5% citric acid (100 mL)
  5. washThe ether layer was washed with water (50 mL)
  6. dry with materialThe ether solution was dried with sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customevaporated
  10. customto yield 4.9 g (75% yield)

Sources & evidence

ORD record
ord-13d3954f675e4108b8c47ab0161f58b2
Source dataset
uspto-grants-2014_06
Patent number
US08742086B2

Reaction notes

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