Potassium Carbonate → HCID 14971261, compound

HRID 466176Notes

Reaction equation

HRID 466176 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8]([CH:11]=[O:12])=[CH:7][C:6]=2[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]([F:31])([F:30])[C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1>CN(C=O)C.O>[F:20][C:21]([F:30])([F:31])[C:22]1[CH:29]=[CH:28][C:25]([CH2:26][O:1][C:2]2[CH:3]=[CH:4][C:5]3[O:10][CH2:9][C:8]([CH:11]=[O:12])=[CH:7][C:6]=3[CH:13]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 47708156-Hydroxychromene-3-carboxaldehyde

Product 1

HCID 14971261HCID 14971261, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The starting material is prepared as follows: A mixture of 6-hydroxy-2H-1-benzopyran-3-carboxaldehyde (2.50 g, 14.2 mmol) and potassium carbonate (3.62 g, 38.4 mmol) in 50 ml of DMF is treated with 4-trifluoromethylbenzyl bromide (3.73 g, 15.6 mmol). The reaction is allowed to proceed overnight at room temperature. The mixture is diluted with water and extracted three times with dichloromethane. The combined organic layers are washed once with water, dried (MgSO4), and evaporated. Purification by silica gel chromatography (20% ethyl acetate/hexane) yields 6-(4-trifluoromethylbenzyloxy)-2H-1-benzopyran-3-carboxaldehyde, m.p. 108°-110° C.

Workup

  1. customThe starting material is prepared
  2. extractionextracted three times with dichloromethane
  3. washThe combined organic layers are washed once with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification by silica gel chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-96c797d9571c4a99956b5e565fbd0c33
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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