Sodium hydride → HCID 54204380, compound

HRID 2084365Notes

Reaction equation

HRID 2084365 reaction equation
[Br-].[OH:2][CH2:3][CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+].[CH2:27]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[CH2:27]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=[CH:5][CH2:4][CH2:3][OH:2])=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 11025793(3-Hydroxypropyl)triphenylphosphonium bromide

Product 1

HCID 54204380HCID 54204380, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In an argon atmosphere, 3-hydroxypropyltriphenylphosphonium bromide (4.02 g) was suspended in dehydrated THF (30 ml); 60% oily sodium hydride (0.4 g) was added, followed by refluxing for 3 hours. To the reaction mixture, a solution of 4-benzyloxybenzaldehyde (2.12 g) in dehydrated THF (7 ml) was added drop by drop, followed by refluxing for 67 hours. After cooling, the insoluble matter was filtered off; the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to yield the titled compound (1.76 g) as colorless crystals.

Workup

  1. temperatureby refluxing for 3 hours
  2. temperatureby refluxing for 67 hours
  3. temperatureAfter cooling
  4. filtrationthe insoluble matter was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-67636fb1524d4902bb477c5435063f26
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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