Hydrochloric Acid → HCID 510828, compound

HRID 1384889Notes

Reaction equation

HRID 1384889 reaction equation
[C:1]([C:4]1[S:5][C:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[Li+].CC([N-]C(C)C)C.C(C1C=CC=CC=1)C.[C:33](OCC)(=[O:39])[C:34]([O:36]CC)=[O:35].Cl>C1COCC1.CCCCCCC.C(OCC)(=O)C>[O:39]=[C:33]([CH2:2][C:1](=[O:3])[C:4]1[S:5][C:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[CH:7][CH:8]=1)[C:34]([OH:36])=[O:35]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 7500EthylbenzeneHCID 2724682Lithium diisopropylamideHCID 21183837HCID 21183837, compound

Product 1

HCID 510828HCID 510828, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.) solution of 2-acetyl-5-(3-fluorobenzyl)thiophene (315 mg, 1.34 mmol) in anhydrous THF (5 mL) under an atmosphere of argon, LDA (0.7 mL, 2 M in a mixture of heptane, THF and ethylbenzene, 1.40 mmol) was added dropwise over a period of 10 min. After the reaction mixture was stirred at −78° C. for an additional 40 min, diethyl oxalate (0.26 mL, 1.91 mmol) was added over a period of 5 min. The resultant mixture was allowed to warm to rt and stirred overnight. The resultant solution was diluted with ethyl acetate, and neutralized with dilute HCl. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was triturated with hexane. The precipitate was filtered to provide the title compound as yellow solid.

Workup

  1. additionwas added dropwise over a period of 10 min
  2. temperatureto warm to rt
  3. stirringstirred overnight
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was triturated with hexane
  10. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-721c3268a21c41bea0d60fd29a2e1a8c
Source dataset
uspto-grants-2001_07
Patent number
US06262055B1

Reaction notes

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