Ethyl Acetate → Diisopropylether ethyl acetate

HRID 1766014Notes

Reaction equation

HRID 1766014 reaction equation
[OH-].[Na+].C(OC([O-])=O)(O[C:6](C)([CH3:8])[CH3:7])=O.C1C2[CH:21]=[C:22]([OH:25])[CH:23]=CC=2CCCN1.[C:26]([O:29][CH2:30][CH3:31])(=[O:28])[CH3:27]>C(Cl)(Cl)Cl.O>[C:26]([O:29][CH2:30][CH3:31])(=[O:28])[CH3:27].[CH:6]([O:25][CH:22]([CH3:21])[CH3:23])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 114479112,3,4,5-Tetrahydro-1H-2-benzazepin-8-OLHCID 22064466Tert-butyldicarbonate

Product 1

HCID 22281796Diisopropylether ethyl acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

2 N sodium hydroxide (40 ml) and t-butyl dicarbonate were added at 0° C. to a solution of 2,3,4,5-tetrahydro-1H-2-benzazepin-8-ol hydrobromate (12.0 g, 49.2 mm) in chloroform (40 ml) and water (40 ml), and the mixture was stirred at room temperature for 16 hours. Ethyl acetate was added to the resulting mixture which was then washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the resultant residues were formed into powder with ethyl acetate-isopropyl ether, to give the title compound (7.99 g).

Workup

  1. washwas then washed with a saturated saline solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-56f238d8cbc3493ea4cf5a10af39710b
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

Loading…