1-Bromohexane → HCID 14971262, compound

HRID 466178Notes

Reaction equation

HRID 466178 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+].[CH2:20](Br)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CN(C=O)C.O>[CH2:20]([O: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)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 81011-Bromohexane2×HCID 11430Potassium Carbonate2×HCID 47708156-Hydroxychromene-3-carboxaldehyde

Product 1

HCID 14971262HCID 14971262, 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 (4.0 g, 22.7 mmol) and potassium carbonate (6.26 g, 45.3 mmol) in 80 ml of DMF is treated with n-hexyl bromide (4.5 g, 27.2 mmol). The mixture is stirred overnight at room temperature. Additional potassium carbonate (3.1 g, 22.4 mmol) and n-hexyl bromide (1.0 g, 6.1 mmol) are added and, after another overnight reaction, no more starting material is detected in the reaction mixture. The reaction mixture is diluted with water and extracted three times with dichloromethane. The combined organic phases are dried (MgSO4) and evaporated. Purification by silica gel chromatography (10% ethyl acetate/hexane) yields 6-(n-hexyloxy)-2H-1-benzopyran-3-carboxaldehyde, m.p. 36°-38° C., which is converted as described above to 3-(N-hydroxyaminomethyl)-6-(n-hexyloxy)-2H-1-benzopyran.

Workup

  1. customThe starting material is prepared
  2. customreaction
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases are dried (MgSO4)
  5. customevaporated
  6. customPurification by silica gel chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-53d595f182f44ddb8674598b1c691d91
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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