Ammonium Chloride → HCID 66587953, compound

HRID 530926

Reaction equation

HRID 530926 reaction equation
[CH:1]1([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH2:3][CH2:2]1.Br[CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1.C([N-]C(C)C)(C)C.[Li+].[Cl-].[NH4+]>CCCCCC.C(OCC)(=O)C.O.C1COCC1>[O:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[O:16][CH2:15][CH2:14][CH2:13][CH2:12][C:1]1([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 5590192-(4-Bromobutoxy)tetrahydro-2H-pyranHCID 2724682Lithium diisopropylamideHCID 13676038tert-Butyl cyclopropanecarboxylate

Product 1

HCID 66587953HCID 66587953, compoundYield 48.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-65 °C

Procedure

Under the argon atmosphere, tert-butyl cyclopropylcarboxylate (3.76 g) and 2-(4-bromobutoxy)tetrahydro-2H-pyran (7.52 g) were dissolved in anhydrous/THF (106 mL), followed by cooling to an inner temperature of −65° C. A lithium diisopropylamide solution (2.0M, THF:heptane:ethylbenzene solution) (19.8 mL) was added dropwise over 15 minutes. After completion of addition, the mixture was stirred at room temperature for 8 hours. An aqueous saturated ammonium chloride solution was added to stop the reaction, and water, and hexane:ethyl acetate (1:1) were added, followed by extraction. The organic layer was washed with dilute hydrochloric acid, water and an aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate. The residue obtained by concentration was purified by silica gel column chromatography (hexane:ethyl acetate, 98:2→90:10) to obtain the title compound (3.86 g) having the following physical property values.

Workup

  1. additionAfter completion of addition
  2. additionwere added
  3. extractionfollowed by extraction
  4. washThe organic layer was washed with dilute hydrochloric acid, water
  5. dry with materialan aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate
  6. customThe residue obtained by concentration
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 98:2→90:10)

Sources & evidence

ORD record
ord-8a9d3c6b9d004ceab18b43b791ed9aa9
Source dataset
uspto-grants-2016_05
Patent number
US09353113B2

Linked notes

Loading…