Hydrochloric Acid → HCID 17860745, compound

HRID 1353147Notes

Reaction equation

HRID 1353147 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].[C:13](Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:13]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12])(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 62493Pivaloyl chlorideHCID 1199215-Hydroxy-1-tetralone

Product 1

HCID 17860745HCID 17860745, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a pyridine (180 ml) solution of 5-hydroxy-1-tetralone (30.0 g), 4-dimethylaminopyridine (1.13 g) was added, and pivaloyl chloride (25.0 ml) was added thereto under ice-cooling, followed by stirring at room temperature overnight. The reaction mixture was ice-cooled, and a concentrated hydrochloric acid was added thereto, followed by extracting with ethyl acetate. The extract was washed with water and saturated saline in this order, dried with anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 5:1) to thereby obtain the title compound (45.4 g) having the following physical data.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooled
  3. extractionby extracting with ethyl acetate
  4. washThe extract was washed with water and saturated saline in this order
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 5:1)

Sources & evidence

ORD record
ord-7e275e88ec1d4ac483d6f2fc83a9160a
Source dataset
uspto-grants-2007_05
Patent number
US07220864B2

Reaction notes

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