Sodium hydride → HCID 53907933, compound

HRID 345898Notes

Reaction equation

HRID 345898 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 53907933HCID 53907933, 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 dropwise to a suspension of sodium hydride (128 mg; a 60% suspension in mineral oil) in tetrahydrofuran (5 ml) at 0° under argon. After 1.5 hours at room temperature, the mixture was cooled to 0° and a solution of 5-trimethylsilyl-3-furaldehyde (450 mg, 2.68 mmol) in tetrahydrofuran (15 ml) was added. Stirring was continued for 14 hours, while the cooling bath attained room temperature. The mixture was quenched with 5% ammonium chloride and washed with 5% sodium bicarbonate and water. Evaporation of the dried (magnesium sulfate) organic phase gave a residue, which was purified by a silica column using 5% ethyl acetate/hexane to give the titled ketone.

Workup

  1. customat 0°
  2. temperaturethe mixture was cooled to 0°
  3. waitwas continued for 14 hours, while the cooling bath attained room temperature
  4. customThe mixture was quenched with 5% ammonium chloride
  5. washwashed with 5% sodium bicarbonate and water
  6. customEvaporation of the
  7. dry with materialdried (magnesium sulfate) organic phase
  8. customgave a residue, which
  9. customwas purified by a silica column

Sources & evidence

ORD record
ord-8d32d059b743444ab6f3961eb26bc22b
Source dataset
uspto-grants-1991_10
Patent number
US05059611

Reaction notes

Loading…