Acetonitrile → HCID 68880526, compound

HRID 50009Notes

Reaction equation

HRID 50009 reaction equation
C[Si](I)(C)C.C(OC([C:11]1([CH:15](O)[C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[CH2:14][CH2:13][CH2:12]1)=O)C.[OH-:22].[Na+].C[CH2:25][O:26]C(C)=O.[CH3:30][C:31]#N>>[CH2:30]([O:22][C:25]([C:15]1([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[CH2:11][CH2:14][CH:13]1[CH3:12])=[O:26])[CH3:31]

Participants

6

Reactant 5

HCID 6342Acetonitrile2×HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 85247Trimethylsilyl iodideHCID 12080529Cyclobutanecarboxylic acid, 1-(hydroxy-2-thienylmethyl)-, ethyl ester

Product 1

HCID 68880526HCID 68880526, compound

Conditions

Temperature
23 °C

Procedure

Trimethylsilyliodide (20 g, 100 mmol) was added to CH3CN (10 mL) at 0° C. and the mixture was allowed to stir 5 min. A solution of alcohol 2 (5 g, 20 mmol) in CH3CN (10 mL) was added slowly while the temperature was kept between 4-10° C. and the reaction was allowed to warm to 23° C. After stirring for 2 h at 23° C. the reaction was judged complete via TLC analysis. The mixture was poured into 3N NaOH at 0° C. and EtOAc was added. The organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. FCC (silica gel, 1:1 hexane/CH2Cl2) gave 2.3 g of the above named ester 3.

Workup

  1. customwas kept between 4-10° C.
  2. stirringAfter stirring for 2 h at 23° C. the reaction
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0217d9ac8db847a3b85531c5faa9f88b
Source dataset
uspto-grants-2004_03
Patent number
US06710072B2

Reaction notes

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