Hydrochloric Acid → HCID 19822188, compound

HRID 1030432Notes

Reaction equation

HRID 1030432 reaction equation
[ClH:1].N([O-])=O.[Na+].[C:6]([O:10][CH2:11][CH3:12])(=[O:9])[CH:7]=[CH2:8].N[C:14]1[CH:45]=[CH:44][C:17]([O:18][CH2:19][C:20]2([CH3:43])[CH2:29][C:28](=[O:30])[C:27]3[C:22](=[C:23]([CH3:42])[C:24]([CH3:41])=[C:25]([O:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:26]=3[CH3:31])[O:21]2)=[CH:16][CH:15]=1>O.CC(C)=O>[C:37]([O:36][C:34]([CH2:33][O:32][C:25]1[C:26]([CH3:31])=[C:27]2[C:22](=[C:23]([CH3:42])[C:24]=1[CH3:41])[O:21][C:20]([CH2:19][O:18][C:17]1[CH:16]=[CH:15][C:14]([CH2:8][CH:7]([Cl:1])[C:6]([O:10][CH2:11][CH3:12])=[O:9])=[CH:45][CH:44]=1)([CH3:43])[CH2:29][C:28]2=[O:30])=[O:35])([CH3:38])([CH3:39])[CH3:40]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 19822282HCID 19822282, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19822188HCID 19822188, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

16 ml of concentrated hydrochloric acid, 7 ml of an aqueous solution containing 3.1 g of sodium nitrite and 37 ml of ethyl acrylate were added, in that order, at 5°-10° C. to a mixture of 16 g of 2-(4-aminophenoxymethyl)-6-t-butoxycarbonylmethoxy-2,5,7,8-tetramethylchroman-4-one (prepared as described in Preparation 62) and 160 ml of acetone. Then 0.5 g of cuprous oxide was added gradually at an internal temperature of 40°-43° C. After about 30 minutes, the evolution of nitrogen had ceased. The reaction mixture was then poured into water and extracted with benzene. This extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled from the extract under reduced pressure, and the residue was purified by silica gel column chromatography eluted with a 9:1 by volume mixture of cyclohexane and ethyl acetate, to give the title compound.

Workup

  1. extractionextracted with benzene
  2. washThis extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled from the
  5. extractionextract under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. washeluted with a 9:1 by volume mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-620caefe70fa44a981849e3b4ce00d87
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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