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Sodium hydride → HCID 19362787, compound

HRID 2393270
Notes
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Reaction equation

HRID 2393270 reaction equation
[H-].[Na+].[CH2:3]([O:10][P:11]([O-:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:21]([C:24]1[CH:31]=[C:30]([CH:32]([CH3:34])[CH3:33])[CH:29]=[C:28]([CH:35]([CH3:37])[CH3:36])[C:25]=1[CH2:26]Br)([CH3:23])[CH3:22].P([O-])([O-])[O-]>O1CCCC1>[CH2:13]([O:12][P:11]([CH2:26][C:25]1[C:24]([CH:21]([CH3:23])[CH3:22])=[CH:31][C:30]([CH:32]([CH3:34])[CH3:33])=[CH:29][C:28]=1[CH:35]([CH3:37])[CH3:36])(=[O:20])[O:10][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 107908Phosphite2×HCID 10590086HCID 10590086, compoundHCID 21904359Dibenzylphosphite

Product 1

HCID 19362787HCID 19362787, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Sodium hydride (2.0 g, 50 mmol), was added in portions to dibenzylphosphite (13.0 g, 50 mmol) in tetrahydrofuran (250 mL) at room temperature. When no further reaction was apparent, added 2,4,6-triisopropylbenzyl bromide (14.47 g, 49 mmol) and stirred at room temperature. Stirred overnight at room temperature, added more phosphite anion (11.94 g phosphite, 1.30 g NaH), and stirred over 2 days at room temperature. The reaction mixture was concentrated, the residue was taken up in ethyl acetate, washed with 10% aqueous citric acid solution, brine, dried (magnesium sulfate), filtered, and concentrated to an oil. The oil was chromatographed on silica gel using 4:1 hexanes/ethyl acetate as eluant. The product was obtained as a solid in two portions, 17.47 g, (73%). Analysis calculated for (C30H39O3P).

Workup

  1. customWhen no further reaction
  2. stirringStirred overnight at room temperature
  3. stirringstirred over 2 days at room temperature
  4. concentrationThe reaction mixture was concentrated
  5. washwashed with 10% aqueous citric acid solution, brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customThe oil was chromatographed on silica gel using 4:1 hexanes/ethyl acetate as eluant
  10. customThe product was obtained as a solid in two portions, 17.47 g, (73%)

Sources & evidence

ORD record
ord-e5640ff6ee82439f80564ac9fb3e2294
Source dataset
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05807846

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes