3-Dipropylamino-5-chloroformyichroman → 3-Dipropylamino-5-acetylchroman

HRID 37649Notes

Reaction equation

HRID 37649 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:15](Cl)=[O:16])[O:7][CH2:6]1)[CH2:2][CH3:3].[CH2:21](N(CCC)C1CC2C(=CC=CC=2C(OC)=O)OC1)CC.[Li]C>O1CCCC1.[Cu]I>[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:15](=[O:16])[CH3:21])[O:7][CH2:6]1)[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 190280843-Dipropylamino-5-chloroformyichromanHCID 190280933-Dipropylamino-5-methyloxycarbonylchromanHCID 178418348HCID 178418348, compound

Product 1

HCID 102212133-Dipropylamino-5-acetylchroman

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

3-Dipropylamino-5-chloroformylchroman*HCl (4.42 g, 13.4 mmol), prepared from 3-dipropylamino-5-methyloxycarbonylchroman (Example 2) analogous to the procedure used in Example 3, in dry tetrahydrofuran (20 ml), was added to a pre-formed solution of lithium dimethylcuprate; prepared from MeLi and CuI, in 200 mL tetrahydrofuran at -78° C. The solution was stirred for 15 minutes at -78° C. and was then allowed to reach room temperature during 10 minutes. Then, 30 mL H20 was slowly added. The organic phase was decanted, dried with Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8. The title compound was crystallized as salt from ethyl acetate. Mp 106°-108° C. (oxalate).

Workup

  1. waitto reach room temperature during 10 minutes
  2. additionThen, 30 mL H20 was slowly added
  3. customThe organic phase was decanted
  4. dry with materialdried with Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8
  7. customThe title compound was crystallized as salt from ethyl acetate

Sources & evidence

ORD record
ord-be46729521be46dc9b9e591301f42c4d
Source dataset
uspto-grants-1995_05
Patent number
US05420151

Reaction notes

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