Sodium hydride → HCID 19991603, compound

HRID 1032281Notes

Reaction equation

HRID 1032281 reaction equation
COP([CH2:7][C:8](=[O:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=O)OC.[H-].[Na+].[CH3:23][Si:24]([CH3:33])([CH3:32])[C:25]1[O:29][CH:28]=[C:27]([CH:30]=O)[CH:26]=1>O1CCCC1>[O:20]=[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])/[CH:7]=[CH:30]/[C:27]1[CH:26]=[C:25]([Si:24]([CH3:33])([CH3:32])[CH3:23])[O:29][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 14883456HCID 14883456, compoundHCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde

Product 1

HCID 19991603HCID 19991603, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of dimethyl-2-oxotridecylphosphonate (984 mg. 3.21 mmol) in tetrahydrofuran (25 ml) was added to a suspension of sodium hydride (78 mg, 3.21 mmol) in tetrahydrofuran (5 ml) at 0° C. (u.c.) under argon. After 30 min, a solution of 5-trimethylsilyl-3-furaldehyde (450 mg. 2.68 mmol) in tetrahydrofuran (15 ml) was added. Stirring was contained overnight while the cooling bath attained room temperature. The reaction mixture was quenched with saturated ammonium chloride and the organic layer separated. Evaporation of the dried (magnesium sulfate) organic layer gave a residue, which was purified by flash chromotography on a silica using 5% ethyl acetate/hexane to give the title compound.

Workup

  1. waitwas contained overnight while the cooling bath attained room temperature
  2. customThe reaction mixture was quenched with saturated ammonium chloride
  3. customthe organic layer separated
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate) organic layer
  6. customgave a residue, which
  7. customwas purified by flash chromotography on a silica using 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-34969900599c4a75961964842a19057d
Source dataset
uspto-grants-1990_09
Patent number
US04957917

Reaction notes

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