Hydrochloric Acid → HCID 59304070, compound

HRID 544804Notes

Reaction equation

HRID 544804 reaction equation
[OH:1][CH:2]([CH3:15])[CH2:3][C:4]([CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH:8]=[C:7]1[CH3:14])=[O:5].CCN(CC)CC.CN(C1C=CC=CN=1)C.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>C(Cl)Cl>[C:32]([O:1][CH:2]([CH3:15])[CH2:3][C:4](=[O:5])[CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH:8]=[C:7]1[CH3:14])(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 23456997HCID 23456997, compound

Product 1

HCID 59304070HCID 59304070, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone (4.00 g, 92% pure, 17.5 mmol), NEt3 (3.2 ml, 22.85 mmol) and dimethylamino pyridine (DMAP) (400 mg) in CH2Cl2 (100 ml) was added benzoylchloride (2.43 ml, 20.94 mmol). The reaction medium was stirred for 65 h at room temperature. Then, the mixture was acidified with 5% aqueous HCl and extracted twice with ether and washed with water, saturated aqueous NaHCO3 and then with saturated aqueous NaCl. Finally, the organic phases were dried over Na2SO4, concentrated at 50-60°/0.03 mbar) and purified by flash-chromatography over SiO2 (cyclohexane/AcOEt=97:3). 4.25 g of product were thus obtained (yield: 73%).

Workup

  1. extractionextracted twice with ether
  2. washwashed with water, saturated aqueous NaHCO3
  3. dry with materialFinally, the organic phases were dried over Na2SO4
  4. concentrationconcentrated at 50-60°/0.03 mbar) and
  5. custompurified by flash-chromatography over SiO2 (cyclohexane/AcOEt=97:3)

Sources & evidence

ORD record
ord-b0b6fc68ac814258985141777bcb3430
Source dataset
uspto-grants-2011_05
Patent number
US07935669B2

Reaction notes

Loading…