Ethylbenzene → HCID 59442588, compound

HRID 657516Notes

Reaction equation

HRID 657516 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N-]C(C)C)(C)C.[Li+].C(C1C=CC=CC=1)C.[O:28]1[C:32]2([CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]2)[O:31][CH2:30][CH2:29]1.C(=O)([O-])O.[Na+]>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([C:35]3([OH:38])[CH2:36][CH2:37][C:32]4([O:31][CH2:30][CH2:29][O:28]4)[CH2:33][CH2:34]3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 7500EthylbenzeneHCID 74581Thiazole, 4-phenyl-HCID 516892Sodium BicarbonateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 2724682Lithium diisopropylamide

Product 1

HCID 59442588HCID 59442588, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-70 °C

Procedure

4.5 g of 4-phenylthiazole were dissolved in 80 ml of anhydrous THF and 18.1 ml of a 2 M solution of lithium diisopropylamide in THF/HEP/ethylbenzene (Aldrich) were added dropwise at −70° C. The mixture was stirred at −70° C. for 60 min, then a solution of 4.4 g of 1,4-dioxaspiro[4.5]decan-8-one in 50 ml of anhydrous THF was added dropwise at −65° C. to −70° C. Subsequently, the mixture was warmed to room temperature, poured onto 120 ml of a saturated aqueous sodium hydrogencarbonate solution and extracted three times with 80 ml each of EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. 7.1 g of the title compound were obtained as a pale yellow oil.

Workup

  1. temperatureSubsequently, the mixture was warmed to room temperature
  2. extractionextracted three times with 80 ml each of EA
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-95ea742fe58c4e289de8fa550bd483a7
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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