Hydrochloric Acid → HCID 70494140, compound

HRID 358359Notes

Reaction equation

HRID 358359 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:15][C@@H:16]1[CH2:23][C@H:22]2[C@H:18]([CH2:19][C:20](=[O:24])[O:21]2)[C@H:17]1/[CH:25]=[CH:26]/[C@@H:27]([OH:33])[CH2:28][C:29]#[C:30][CH2:31][CH3:32])(=O)C1C=CC=CC=1.Cl>CO>[OH:33][C@@H:27]([CH2:28][C:29]#[C:30][CH2:31][CH3:32])/[CH:26]=[CH:25]/[C@H:17]1[C@H:16]([OH:15])[CH2:23][C@H:22]2[C@@H:18]1[CH2:19][C:20](=[O:24])[O:21]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 70482763HCID 70482763, compound

Product 1

HCID 70494140HCID 70494140, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

712 mg of anhydrous potassium carbonate are introduced into a solution of 4.3 g of the alcohol prepared in Example (23d) in 47 ml of methanol and the mixture is stirred at room temperature for 3 hours. While cooling with ice, 0.72 ml of concentrated hydrochloric acid are then added dropwise to the reaction solution and the whole is concentrated in vacuo. The residue is dissolved in methylene chloride, the solution is dried over magnesium sulphate and concentrated in vacuo. The crude product is chromatographed over silica gel by gradient elution in methylene chloride/acetone. 2.85 g of the title compound are obtained.

Workup

  1. additionare then added dropwise to the reaction solution
  2. concentrationthe whole is concentrated in vacuo
  3. dissolutionThe residue is dissolved in methylene chloride
  4. dry with materialthe solution is dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is chromatographed over silica gel by gradient elution in methylene chloride/acetone

Sources & evidence

ORD record
ord-6707d13c4f9d44768aea6ce5dda336d4
Source dataset
uspto-grants-1984_08
Patent number
US04466969

Reaction notes

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