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Tin tetrachloride → HCID 15490887, Verbindung

HRID 1954257
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1954257
[CH:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7]([OH:9])=O)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[CH2:26]([C:33]1[S:34][C:35]([CH3:39])=[C:36]([CH3:38])[CH:37]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH2:26]([C:33]1[S:34][C:35]([CH3:39])=[C:36]([CH3:38])[C:37]=1[C:7]([C:6]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=1)=[O:9])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 102419632,3-Dimethyl-5-benzylthiopheneHCID 150525974-Methoxy-3-isopropylbenzoic acid

Produkt 1

HCID 15490887HCID 15490887, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

At ambient temperature, to a stirred solution containing 3-isopropyl-4-methoxybenzoic acid (27.00 g, 0.139 mol, RN-33537-78-9) and oxalyl chloride (13.3 mL, 0.153 mol) in CH2Cl2 (460 mL) was added N,N-DMF (5 drops). After 2 h, the reaction was cooled to -78° C. To the reaction was added tin (IV) chloride (17.89 mL, 0.153 mol) followed by a solution of 2-benzyl-4,5-dimethylthiophene (28.12 g, 0.139 mol) in CH2Cl2 (120 mL) that had been previously cooled to -78° C. After the addition was complete, the dry ice/acetone bath was removed and the reaction was stirred for 18 h, eventually warming to ambient temperature. The reaction was quenched into H2O (2 L) and extracted with ether. The combined ethereal extracts were sequentially washed with 1N HCl (3×500 mL), H2O (2×500 mL), NaHCO3 (2×500 mL), brine (1×500 mL), dried (MgSO4) and concentrated. Purification on silica gel, eluting with 5% EtOAc/pet. ether, gave 43.65 g (83%) of the title compound as an oil. 1H NMR (DMSO-d6) δ 1.13 (s, 3 H), 1.15 (s, 3 H), 1.81 (s, 3 H), 2.26 (s, 3 H), 3.23 (q, 1 H), 3.85 (s, 2 H), 3.88 (s, 3 H), 7.04-7.24 (m, 6 H), 7.55 (dd, 1 H), 7.63 (d, 1 H).

Aufarbeitung

  1. temperaturehad been previously cooled to -78° C
  2. additionAfter the addition
  3. customthe dry ice/acetone bath was removed
  4. temperatureeventually warming to ambient temperature
  5. customThe reaction was quenched into H2O (2 L)
  6. extractionextracted with ether
  7. washThe combined ethereal extracts were sequentially washed with 1N HCl (3×500 mL), H2O (2×500 mL), NaHCO3 (2×500 mL), brine (1×500 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customPurification on silica gel
  11. washeluting with 5% EtOAc/pet. ether

Quellen und Nachweise

ORD-Eintrag
ord-8faf2e2c1beb4d3dae055c0c7d3d2f43
Quelldatensatz
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06121271

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