Hydrochloric Acid → HCID 54553760, compound

HRID 1741973Notes

Reaction equation

HRID 1741973 reaction equation
[OH:1][CH2:2][CH:3]1[CH:8]2[O:9][C:10]([CH3:13])([CH3:12])[O:11][CH:7]2[CH:6]([O:14][CH:15]([O:17][CH2:18][CH3:19])[CH3:16])[CH2:5][C:4]1=[O:20].C(N(CC)CC)C.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29].Cl>C(Cl)Cl>[Si:28]([O:1][CH2:2][CH:3]1[CH:8]2[O:9][C:10]([CH3:12])([CH3:13])[O:11][CH:7]2[CH:6]([O:14][CH:15]([O:17][CH2:18][CH3:19])[CH3:16])[CH2:5][C:4]1=[O:20])([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 19011015HCID 19011015, compound

Product 1

HCID 54553760HCID 54553760, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Hydroxymethyl-3,4-(dimethylmethylenedioxy)-5-(1-ethoxyethoxy)cyclohexanone (765 mg) was dissolved in 7 ml of dry methylene chloride, and 1.2 ml of triethylamine, 55.6 mg of N,N-dimethylaminopyridine and 520 mg of tert-butyldimethylsilyl chloride were added at 0° C., followed by stirring the mixture at 0° C. for 13 hours. The obtained reaction mixture was poured into 1N hydrochloric acid, and extracted with diethyl ether. The extract was washed with a saturated sodium hydrogen carbonate aqueous solution and then with a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 1.04 g of 2-(tert-butyldimethylsilyloxymethyl)-3,4-(dimethylmethylenedioxy)-5-(1-ethoxyethoxy)cyclohexanone having the following properties.

Workup

  1. customThe obtained reaction mixture
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with a saturated sodium hydrogen carbonate aqueous solution
  4. dry with materialwith a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4378f324346645c796e3620888603d08
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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