Potassium Carbonate → HCID 86621473, compound

HRID 2241055Notes

Reaction equation

HRID 2241055 reaction equation
Br[CH2:2][CH2:3][O:4][C:5](=[O:7])[CH3:6].[CH2:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:17]2[CH2:22][C:21]([CH3:24])([CH3:23])[CH2:20][C:19]([CH3:26])([CH3:25])[CH2:18]2)=[CH:12][C:11]=1[OH:33])C.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:8][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:17]2[CH2:22][C:21]([CH3:23])([CH3:24])[CH2:20][C:19]([CH3:26])([CH3:25])[CH2:18]2)=[CH:12][C:11]=1[O:33][CH2:6][C:5]([O:4][CH2:3][CH3:2])=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 68500262HCID 68500262, compound

Product 1

HCID 86621473HCID 86621473, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
100 °C

Procedure

Bromoethylacetate (187 mg, 1.12 mmol), compound 41 (150 mg, 0.449 mmol), and K2CO3 (185 mg, 1.34 mmol) were combined with dry acetone (5 mL) in a sealed microwave vessel. The mixture was heated at 100° C. for 20 minutes in a Personal Chemistry Emrys Optimizer microwave. The reaction was allowed to cool to room temperature and the solids filtered. The solids were rinsed twice with acetone and the solvent was removed in vacuuo to give 187 mg (99%) of compound 42. The crude material was used without additional purification. 1H NMR (400 MHz, CDCl3): δ 0.88 (s, 6H), 0.91 (s, 6H), 1.20-1.25 (m, 5H), 1.75 (s, 2H), 1.90 (s, 2H), 2.23 (s, 3H), 4.22 (m, 3H), 4.46 (s, 2H), 6.73 (d, J=8.3 Hz, 1H), 6.75-7.05 (m, 2H), 7.09-7.46 (m, 5H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe solids filtered
  3. washThe solids were rinsed twice with acetone
  4. customthe solvent was removed in vacuuo

Sources & evidence

ORD record
ord-f6b0536769d94d24a119862568f248fa
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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