Potassium Carbonate → HCID 54202012, compound

HRID 1728428Notes

Reaction equation

HRID 1728428 reaction equation
C(=O)([O-])[O-].[K+].[K+].CC(C)(C)C([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([O:30][CH3:31])=[C:19]2[CH:26]3[CH2:27][CH:22]4[CH2:23][C:24]([Cl:29])([CH2:28][CH:20]2[CH2:21]4)[CH2:25]3)[CH:13]=1)=O>CO>[CH3:31][O:30][C:18](=[C:19]1[CH:20]2[CH2:21][CH:22]3[CH2:23][C:24]([Cl:29])([CH2:25][CH:26]1[CH2:27]3)[CH2:28]2)[C:14]1[CH:13]=[C:12]([OH:11])[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 54198636HCID 54198636, compound

Product 1

HCID 54202012HCID 54202012, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The combined pivaloyl ester fractions (5.5 g, 14.1 mmol) were taken up in 40 ml of methanol and refluxed with 5.37 g of anhydrous potassium carbonate for 40 minutes. The residue remaining after the methanol was stripped off was partitioned between water and 30% ethyl acetate-hexanes, and the organic fractions were concentrated and plug filtered on a short silica gel column to give 4.07 g (88% yield based on 5-chloroadamantan-2-one) of 3-(methoxy-5-chlorotricyclo[3.3.1.13,7 ]dec-2-ylidenemethyl) phenol as a crispy white foam which became slightly tacky upon exposure to air.

Workup

  1. customwas partitioned between water and 30% ethyl acetate-hexanes
  2. concentrationthe organic fractions were concentrated
  3. filtrationplug filtered on a short silica gel column

Sources & evidence

ORD record
ord-5f9b50fc3aaf4550b1f4097531d7eb7c
Source dataset
uspto-grants-1994_07
Patent number
US05326882

Reaction notes

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