Diethyl Ether → 1-(3,5,5-Trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

HRID 2240803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240803
[CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[C:4]2[CH2:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:3]=12.[CH2:16](OCC)C>C[Li]>[CH3:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:16])=[C:4]2[CH2:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:3]=12

Komponenten

4

Edukt 2

HCID 3283Diethyl EtherHCID 57508884HCID 57508884, Verbindung

Produkt 1

HCID 574374241-(3,5,5-Trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418348HCID 178418348, VerbindungLösungsmittel

Reaktionsbedingungen

Temperatur
26 °C

Versuchsvorschrift

To a suspension of 3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (4.10 g, 18.28 mmol) in diethyl ether (300 mL), methyllithium (23 mL, 1.6 M solution in diethyl ether) is slowly added at rt. The reaction mixture becomes clear, yellow and slightly warm (26° C.), and is stirred for 15 min before it is quenched with water. The organic layer is separated, washed once more with water, dried over MgSO4 and evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (2.80 g) as a pale yellow crystalline solid; LC-MS: tR=1.06 min, [M+1]=223.17; 1H NMR (CDCl3): δ 3.00 (t, J=7.0 Hz, 2H), 2.43 (s, 3H), 2.31 (s, 3H), 2.26 (s, 2H), 1.51 (t, J=7.0 Hz, 2H), 0.95 (s, 6H).

Aufarbeitung

  1. additionis slowly added at rt
  2. customis quenched with water
  3. customThe organic layer is separated
  4. washwashed once more with water
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Quellen und Nachweise

ORD-Eintrag
ord-a7faafd70ea24f9bb67eae8829cbf4ee
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723378B2

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