Sodium hydride → 4-[2-(4-Bromophenyl)vinyl]-4-(t-butyldimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazole

HRID 1375922Notes

Reaction equation

HRID 1375922 reaction equation
[Br-].[Br:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[H-].[Na+].[Si:31]([O:38][CH2:39][C:40]1([CH:46]=O)[CH2:44][O:43][C:42]([CH3:45])=[N:41]1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>C1COCC1>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[CH:46][C:40]2([CH2:39][O:38][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH2:44][O:43][C:42]([CH3:45])=[N:41]2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2724858[(4-Bromophenyl)methyl]triphenylphosphanium bromideHCID 58787875HCID 58787875, compound

Product 1

HCID 694272274-[2-(4-Bromophenyl)vinyl]-4-(t-butyldimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of (4-bromobenzyl)triphenyl-phosphonium bromide (6 mmol) in dry THF (25 mL) is added NaH (6 mmol) in portions. After stirring at room temperature for 30 min, a solution of 4-(t-butyidimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazole-4-carbaldehyde (prepared according to Scheme 3 using well-known chemistry in the art) (5 mmol) in THF (10 mL) is added in one portion. The mixture is stirred at room temperature for 12 h. After concentration, the residue is treated with EtOAc/hexane (1/5) (100 mL) and the solid is filtrated. The filtrate is washed with brine and dried over Na2SO4. After concentration, the crude product is purified by column chromatography by EtOAc/hexane (1/5) to give the desired product as a colorless oil. MS: (ES+): 410.1 (M+1)+.

Workup

  1. additionis added in one portion
  2. stirringThe mixture is stirred at room temperature for 12 h
  3. concentrationAfter concentration
  4. additionthe residue is treated with EtOAc/hexane (1/5) (100 mL)
  5. filtrationthe solid is filtrated
  6. washThe filtrate is washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationAfter concentration
  9. customthe crude product is purified by column chromatography by EtOAc/hexane (1/5)

Sources & evidence

ORD record
ord-c01446a4631e4b00ba1f819272a51edf
Source dataset
uspto-grants-2007_01
Patent number
US07169817B2

Reaction notes

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