Tetrahydrofuran → HCID 69961754, compound

HRID 742097Notes

Reaction equation

HRID 742097 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([CH2:10][C:11](=P(OCC)OCC)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[Br:24][C:25]1[CH:32]=[CH:31][C:30](OC(C)C)=[CH:29][C:26]=1[CH:27]=O.[CH2:37]1[CH2:41]OC[CH2:38]1>>[C:3]([O:7][C:8](=[O:9])[CH2:10]/[C:11](/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:27]\[C:26]1[CH:29]=[C:30]([CH:37]([CH3:41])[CH3:38])[CH:31]=[CH:32][C:25]=1[Br:24])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 10933678HCID 10933678, compoundHCID 178471742HCID 178471742, compound

Product 1

HCID 69961754HCID 69961754, compoundYield 61%

Conditions

Temperature
0 °C

Procedure

To a suspension of 1.85 g (77.1 mmol) NaH in 130 mL dry THF, 25.4 g (75.1 mmol) tert-butoxycarbonyl-1-ethoxycarbonylethylidendiethoxy-phosphorane (2) was added dropwise at 0° C., The reaction mixture was stirred for 6 h at 0° C. under Ar. This solution was added under Ar dropwise at 0° C. to 15.5 g (63.5 mmol) 2-bromo-5-isopropoxy-benzaldehyde (1), dissolved in 80 mL dry THF. The cooling bath was removed and the reaction mixture was stirred overnight at room temperature. 20 mL water was added and the solvent was removed under reduced pressure. The residue was partitioned between water and dichloromethane. The organic layers were dried (MgSO4), filtered and the solvent was removed under reduced pressure to afford 16.5 g (61%) (E)-3-carboethoxy-4-(2'-bromo-5-isopropylphenyl) -3-butenic acid-tert-butyl ester as a yellow oil.

Workup

  1. additionwas added dropwise at 0° C.
  2. customThe cooling bath was removed
  3. stirringthe reaction mixture was stirred overnight at room temperature
  4. addition20 mL water was added
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was partitioned between water and dichloromethane
  7. dry with materialThe organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9412bd45f2d34d18aeb12f863e65ba4c
Source dataset
uspto-grants-1996_09
Patent number
US05552550

Reaction notes

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