Sodium hydride → HCID 86754379, compound

HRID 1584589Notes

Reaction equation

HRID 1584589 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[N:12]([CH2:13][C:14]2[C:22]([Cl:23])=[CH:21][C:17]3[O:18][CH2:19][O:20][C:16]=3[CH:15]=2)[C:11]([CH2:24][CH2:25][CH3:26])=[N:10][C:9]=1[CH:27]=O)=[O:7])[CH3:4]>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[Cl:23][C:22]1[C:14]([CH2:13][N:12]2[C:8]([C:6]([O:5][CH2:3][CH3:4])=[O:7])=[C:9](/[CH:27]=[CH:13]/[C:14]3[CH:22]=[CH:21][CH:17]=[CH:16][CH:15]=3)[N:10]=[C:11]2[CH2:24][CH2:25][CH3:26])=[CH:15][C:16]2[O:20][CH2:19][O:18][C:17]=2[CH:21]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 21224828HCID 21224828, compound

Product 1

HCID 86754379HCID 86754379, compoundYield 153.9%

Reagents, catalysts & solvents 2

HCID 70671Benzyltriphenylphosphonium chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

150 mg of sodium hydride is added to a suspension containing 1.2 g of benzyltriphenyl phosphonium chloride in 30 ml of tetrahydrofuran. Agitation is carried out for 30 minutes, the reaction medium is cooled down to +10 C and 1 g of the aldehyde obtained in Example 44 in solution in tetrahydrofuran is added and agitation is continued for 2 hours at ambient temperature, followed by filtration, the organic phase is washed with tetrahydrofuran, the solvent is eliminated under reduced pressure and the residue is chromatographed on silica (eluant: CH2Cl2 -AcOEt 80-20). 920 mg of expected product is obtained. M.p.=161° C.

Workup

  1. additionis added
  2. waitagitation is continued for 2 hours at ambient temperature
  3. filtrationfollowed by filtration
  4. washthe organic phase is washed with tetrahydrofuran
  5. customthe residue is chromatographed on silica (eluant: CH2Cl2 -AcOEt 80-20)

Sources & evidence

ORD record
ord-8552d3fa8633479cb1acad2a430b74c2
Source dataset
uspto-grants-1999_08
Patent number
US05932741

Reaction notes

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