(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid → (1aS,5aR)-1-(1,1,2-Trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone

HRID 1924818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1924818
[CH3:1][C:2]1([CH3:15])[C@@H:4]2[CH2:5][C:6]3[C:10]([C@H:3]12)=[C:9]([CH3:11])[S:8][C:7]=3[C:12]([OH:14])=O.[Li][CH3:17]>CCOCC>[CH3:15][C:2]1([CH3:1])[C@@H:4]2[CH2:5][C:6]3[C:10]([C@H:3]12)=[C:9]([CH3:11])[S:8][C:7]=3[C:12](=[O:14])[CH3:17]

Komponenten

4

Edukt 2

HCID 57892448(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acidHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 59380608(1aS,5aR)-1-(1,1,2-Trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanoneAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid (220 mg, 1.00 mmol) in Et2O (10 mL) is added a solution of MeLi (1.6 M, 1.4 mL, 2.10 mmol) in Et2O at such a pace that the reaction mixture is refluxing gently. Upon completion of the addition, stirring is continued at rt for 30 min. The reaction is quenched by adding sat. aq. NH4Cl (3 mL). The organic layer is separated, dried over Na2SO4 and the solvent is evaporated to give (1aS,5aR)-1-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone (165 mg) as a pale yellow oil; LC-MS: tR=1.03 min, [M+1]+=221.20; 1H NMR (CDCl3): δ 3.00 (ddd, J=1.8, 4.7, 18.8 Hz, 1H), 2.80 (d, J=18.8 Hz, 1H), 2.38 (s, 6H), 1.93-1.90 (m, 2H), 1.14 (s, 3H), 0.74 (s, 3H).

Aufarbeitung

  1. temperatureis refluxing gently
  2. additionUpon completion of the addition
  3. customThe reaction is quenched
  4. additionby adding sat. aq. NH4Cl (3 mL)
  5. customThe organic layer is separated
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ddf37fcce97b4831837d79872724b8bc
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178562B2

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