Tetrahydrofuran → HCID 22313292, compound

HRID 965842Notes

Reaction equation

HRID 965842 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][C:8]=1[CH:18]=O)[CH:4]=[CH2:5].[CH2:20]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOC(C)=O>[CH2:3]([O:6][C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][C:8]=1[CH:18]=[CH2:20])[CH:4]=[CH2:5]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 22313405HCID 22313405, compound

Product 1

HCID 22313292HCID 22313292, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of sodium hydride [588 mg (60% oil dispersion), 15 mmol), which had been previously washed with pentane (3×), in THF (30 mL) in a 0° C. ice bath is added methyl triphenylphosphonium bromide (4.6 g, 13 mmol). The suspension is allowed to warm to rt and stir for 30 min. A solution of ethyl 4-(allyloxy)-3-formylbenzoate (2.3 g, 9.8 mmol) in THF (10 mL) is added via canula. The mixture is stirred at rt 2 h. The mixture is diluted with EtOAc and washed with brine. The organic layer is dried of MgSO4, filtered and concentrated in vacuo to a yellow residue. The crude product is purified by flash chromatography on SiO2. Elution with hexanes-EtOAc (95:5) gives 1.8 g (79%) of ethyl 4-(allyloxy)-3-vinylbenzoate as a clear oil: 1H NMR (400 MHz, CDCl3) δ 8.2, 7.9, 7.1, 6.9, 6.1, 5.9, 5.5, 5.3, 4.7, 4.4, 1.4.

Workup

  1. washhad been previously washed with pentane (3×), in THF (30 mL) in a 0° C. ice bath
  2. stirringThe mixture is stirred at rt 2 h
  3. washwashed with brine
  4. dry with materialThe organic layer is dried of MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a yellow residue
  7. customThe crude product is purified by flash chromatography on SiO2
  8. washElution with hexanes-EtOAc (95:5)

Sources & evidence

ORD record
ord-26718a3c95504c4ebc3f1938dd41ecdb
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

Loading…