Sodium Hydroxide → HCID 102041455, compound

HRID 576510Notes

Reaction equation

HRID 576510 reaction equation
CS([O:5][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH2:9]3)O1)[CH2:13]2)(=O)=O.[Cl-].[Cl-].[Cl-].[Al+3].[OH-].[Na+]>ClCCCl.O.C1COCC1>[O:5]=[C:6]1[CH2:15][CH:10]2[CH2:11][CH:12]([CH2:14][C:8]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:9]2)[CH2:13]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 75274483HCID 75274483, compound

Product 1

HCID 102041455HCID 102041455, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of mesylate (3) (1.435 g, 4.5 mmol) and anhydrous aluminium trichloride (720 mg, 5.4 mmol) in distilled 1,2-dichloroethane (12 mL) was stirred was stirred under argon at reflux temperature for 10 min then cooled to r.t. The reaction mixture was diluted with water (24 mL) and THF (24 mL), made basic with 5 M NaOH (30 mL) and stirred at r.t. 30 min before extraction with DCM (2×50 mL), then with AcOEt (2×50 mL). The combined organic layers were dried with MgSO4 and concentrated under reduced pressure to afford a pale yellow oil. Purification by flash chromatography (AcOEt/cyclohexane 0/10 to 3/7, v/v) afforded the desired enone (4) as colorless oil (920 mg, 92%).

Workup

  1. stirringwas stirred under argon
  2. temperatureat reflux temperature for 10 min
  3. stirringstirred at r.t
  4. extraction30 min before extraction with DCM (2×50 mL)
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford a pale yellow oil
  8. customPurification by flash chromatography (AcOEt/cyclohexane 0/10 to 3/7, v/v)

Sources & evidence

ORD record
ord-cd48d14ca07b409d98ba85d6c048730f
Source dataset
uspto-grants-2015_05
Patent number
US09040506B2

Reaction notes

Loading…