Sodium hydride → HCID 76843166, compound

HRID 1391734Notes

Reaction equation

HRID 1391734 reaction equation
[Cl-].[CH2:2]([O:4][C:5](=[O:35])[CH2:6][O:7][C:8]1[CH:33]=[CH:32][C:11]([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:10][C:9]=1[CH3:34])[CH3:3].[H-].[Na+].[Br:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH:42]=O>C1COCC1>[Br:38][C:39]1[CH:40]=[C:41]([CH:42]=[CH:12][C:11]2[CH:32]=[CH:33][C:8]([O:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:35])=[C:9]([CH3:34])[CH:10]=2)[CH:44]=[CH:45][CH:46]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 765833-BromobenzaldehydeHCID 16109177[4-(2-Ethoxy-2-oxoethoxy)-3-methylbenzyl](triphenyl)phosphonium chloride

Product 1

HCID 76843166HCID 76843166, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of [4-(2-ethoxy-2-oxoethoxy)-3-methylbenzyl](triphenyl)phosphonium chloride (500 mg, 0.99 mmol) in dry THF (10 mL) was cooled to 0° C. (ice/water bath) and treated with NaH (44 mg of a 60% dispersion in mineral oil, 1.10 mmol) portion-wise over 5 minutes. The resulting yellow suspension was stirred for 15 minutes and was then treated with 3-bromobenzaldehyde (184 mg, 0.99 mmol) in dry THF (5 mL). The resulting white suspension was allowed to warm to rt over 3.5 hours and was then heated at reflux for 1 hour. The reaction mixture was then allowed to cool to rt, stirred overnight and was then reduced under vacuum. The residue was then partitioned between CHCl3 (20 mL) and water (20 mL) and the layers separated. The cloudy organic layer was dried through a hydrophobic frit and then concentrated to a cream coloured gum (700 mg). Purification by SPE (silica) eluting with cyclohexane:EtOAc (9:1) afforded the title compound (mixture of E:Z isomers) (258 mg).

Workup

  1. temperaturewas then heated
  2. temperatureat reflux for 1 hour
  3. temperatureto cool to rt
  4. stirringstirred overnight
  5. customThe residue was then partitioned between CHCl3 (20 mL) and water (20 mL)
  6. customthe layers separated
  7. customThe cloudy organic layer was dried through a hydrophobic frit
  8. concentrationconcentrated to a cream coloured gum (700 mg)
  9. customPurification by SPE (silica)
  10. washeluting with cyclohexane:EtOAc (9:1)

Sources & evidence

ORD record
ord-aabda56951a044b2bfbeebabd530c9b1
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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