Hydrochloric Acid → HCID 19822181, compound

HRID 1030397Notes

Reaction equation

HRID 1030397 reaction equation
[ClH:1].[C:2]([O:5][C:6]1[C:7]([CH3:32])=[C:8]2[C:13](=[C:14]([CH3:17])[C:15]=1[CH3:16])[O:12][C:11]([CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27](N)=[CH:26][CH:25]=1)([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:10][C:9]2=[O:31])(=[O:4])[CH3:3].N([O-])=O.[Na+].[C:37]([O:41][CH2:42][CH3:43])(=[O:40])[CH:38]=[CH2:39]>O.CC(C)=O>[C:2]([O:5][C:6]1[C:7]([CH3:32])=[C:8]2[C:13](=[C:14]([CH3:17])[C:15]=1[CH3:16])[O:12][C:11]([CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:39][CH:38]([Cl:1])[C:37]([O:41][CH2:42][CH3:43])=[O:40])=[CH:26][CH:25]=1)([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:10][C:9]2=[O:31])(=[O:4])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 19822264HCID 19822264, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19822181HCID 19822181, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

1.5 ml of concentrated hydrochloric acid was added to mixture of 1.1 g of 6-acetoxy-2-(4-aminophenoxymethyl)-2-isobutyl-5,7,8-trimethylchroman-4-one (prepared as described in Preparation 8) and 20 ml of acetone under a nitrogen stream and at room temperature. This was followed by 0.8 g of sodium nitrite and 0.3 ml of water, and then by 4 g of ethyl acrylate. 0.1 g of cuprous oxide was added at room temperature to the reaction mixture, which was then stirred for 1 hour. Water was then added, and the mixture was extracted with benzene. The benzene extract was washed with water and dried over anhdyrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using a 5.1 by volume mixture of hexane and ethyl acetate as eluent, to give the title compound.

Workup

  1. customat room temperature
  2. extractionthe mixture was extracted with benzene
  3. extractionThe benzene extract
  4. washwas washed with water
  5. dry with materialdried over anhdyrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. additionby volume mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-a9445abb756840cba8150cd5b572f204
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

Loading…