Hydrochloric Acid → HCID 12794388, compound

HRID 1499035Notes

Reaction equation

HRID 1499035 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:10](O[Na])([CH3:13])([CH3:12])[CH3:11].C1C[O:19]CC1.Cl.[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:10]12([C:13](=[O:19])[CH2:2][C:1]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:3])[CH2:28][CH:22]3[CH2:27][CH:26]([CH2:25][CH:24]([CH2:23]3)[CH2:11]1)[CH2:12]2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 7410AcetophenoneHCID 8028TetrahydrofuranHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 12794388HCID 12794388, compoundYield 4%

Conditions

Temperature
80 °C

Procedure

Into a flask equipped with a reflux pipe were put 14.50 g of acetophenone, 25.13 g of 1-adamantanecarboxylic acid ethyl, 22 g of tert-butoxysodium, and 60 mL of THF, and the air in the flask was replaced by nitrogen. This reaction container was heated at 80° C. for 7 hours and 30 minutes. Dilute hydrochloric acid was added to this reaction solution, and extraction was performed with toluene. The solvent of the obtained toluene solution was distilled off, and then the obtained residue was purified by flash column chromatography (silica gel) using a mixed solvent of dichloromethane and hexane as a developing solvent in a volume ratio of 9:1, to give 1-(1-adamantyl)-3-phenyl-propane-1,3-dione (colorless oily substance, 4% in yield). The synthesis scheme of Step 1 is shown by (a-4).

Workup

  1. customInto a flask equipped with a reflux pipe
  2. distillationThe solvent of the obtained toluene solution was distilled off
  3. customthe obtained residue was purified by flash column chromatography (silica gel)

Sources & evidence

ORD record
ord-3e1169782a9e4e45a14a59c0da054cda
Source dataset
uspto-grants-2015_12
Patent number
US09200022B2

Reaction notes

Loading…