Cesium carbonate → 3-Benzyloxy-2-cyclopropylmethoxy-benzaldehyde

HRID 253450Notes

Reaction equation

HRID 253450 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([OH:17])=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:24]1([CH2:27]Br)[CH2:26][CH2:25]1.[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10]([O:17][CH2:27][CH:24]2[CH2:26][CH2:25]2)=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 81503BromomethylcyclopropaneHCID 112876163-(Benzyloxy)-2-hydroxybenzaldehyde

Product 1

HCID 598038783-Benzyloxy-2-cyclopropylmethoxy-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 3-benzyloxy-2-hydroxy-benzaldehyde (129, 1.0 g, 4.38 mmol) and cesium carbonate (2.14 g, 6.57 mmol) in N,N-dimethylformamide (50 mL), cyclopropylmethyl bromide (1.77 g, 13.1 mmol) was added at room temperature. The mixture was stirred at 40° C. for 3 days. The reaction mixture was poured into a solution of saturated ammonium chloride and was extracted with ethyl acetate. The organic layer was collected, washed with brine, and dried over magnesium sulfate. After removal of solvent, a viscous liquid was obtained (130, 1.21 g, 98%).

Workup

  1. additionwas added at room temperature
  2. extractionwas extracted with ethyl acetate
  3. customThe organic layer was collected
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of solvent
  7. customa viscous liquid was obtained (130, 1.21 g, 98%)

Sources & evidence

ORD record
ord-9b987b09b5dd49d0b10a4bec644e2d0a
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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