Thiourea → Di-tert-butyl (3-fluoro-4-formylphenyl)(methyl)malonate

HRID 1172885Notes

Reaction equation

HRID 1172885 reaction equation
[C:1]([O:5][C:6](=[O:28])[C:7]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]2OCC[O:23]2)=[C:18]([F:27])[CH:17]=1)([CH3:15])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].NC(N)=S>CCO.O>[F:27][C:18]1[CH:17]=[C:16]([C:7]([CH3:15])([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:28])[CH:21]=[CH:20][C:19]=1[CH:22]=[O:23]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 57443965Di-tert-butyl [4-(1,3-dioxolan-2-yl)-3-fluorophenyl](methyl)malonate

Product 1

HCID 57443966Di-tert-butyl (3-fluoro-4-formylphenyl)(methyl)malonate

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Di-tert-butyl[4-(1,3-dioxolan-2-yl)-3-fluorophenyl](methyl)malonate (0.91 g, 2.30 mmol) and thiourea (0.87 g, 11.4 mmol) were stirred in refluxing EtOH/H2O (6.7 mL/6.7 mL) for 7 hours. Room temperature was attained and the solvent removed in vacuo. H2O (100 mL) was added to the residue and the products extracted into EtOAc (2×100 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo to give the clean product (pale yellow gum). 1H NMR (CDCl3) δ 10.33 (s, 1H), 7.82 (t, J=8.1 Hz, 1H), 7.31 (dd, J=8.1, 1.8 Hz. 1H). 7.27 (dd, J=12.0, 1.8 Hz, 1H), 1.77 (s, 3H), 1.46 (s, 18H).

Workup

  1. customRoom temperature
  2. customthe solvent removed in vacuo
  3. additionH2O (100 mL) was added to the residue
  4. extractionthe products extracted into EtOAc (2×100 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto give the clean product (pale yellow gum)

Sources & evidence

ORD record
ord-4f5c2d4e0b46464095bbd3a299a27563
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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