Diethyl Ether → HCID 10911866, compound

HRID 1654757Notes

Reaction equation

HRID 1654757 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1.C(OCC)C>O1CCCC1.O>[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])[OH:24])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 74794-(Dimethylamino)BenzaldehydeHCID 66111TrimethylsilylacetyleneHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 10911866HCID 10911866, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Place lithium hexamethyldisilazane (12 mL of a 1M solution in tetrahydrofuran, 12 mmol) under an argon atmosphere and cool to 0° C. Add trimethylsilylacetylene (1.7 mL, 12 mmol) and stir for 1 hour at 0° C. Add 4-dimethylaminobenzaldehyde (1.49 g, 10 mmol) in tetrahydrofuran (25 mL). Allow to warm to room temperature and stir for 3 hours. Pour the mixture into ethyl ether and water, separate the organic phase and evaporate the solvent in vacuo. Filter the oil through silica gel (20% ethyl acetate/hexane) and evaporate the solvent in vacuo to yield 2.26 g of the title compound.

Workup

  1. customseparate the organic phase
  2. customevaporate the solvent in vacuo
  3. filtrationFilter the oil through silica gel (20% ethyl acetate/hexane)
  4. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-bfab94a218b14ef18a2c9a1b294216f0
Source dataset
uspto-grants-1995_04
Patent number
US05409942

Reaction notes

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