1,3-Propanedithiol → Ethyl (E)-4-[-2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-(1,3-dithian-2-yl)naphthalen-2-yl)ethenyl]benzoate

HRID 1953870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1953870
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9](=O)[C:8]2[CH:7]=[C:6](/[CH:13]=[CH:14]/[C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]1=2.[CH3:27]C1(C)CCC(=O)C2C=C(/C=C/C3C=CC(C(O)=O)=CC=3)C=CC1=2.[CH2:51]([SH:55])[CH2:52][CH2:53][SH:54]>C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][CH:9]([CH:27]2[S:55][CH2:51][CH2:52][CH2:53][S:54]2)[C:8]2[CH:7]=[C:6](/[CH:13]=[CH:14]/[C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH:5]=[CH:4][C:3]1=2

Komponenten

6

Edukt 3

HCID 80131,3-PropanedithiolHCID 12069038Ethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethenyl]-benzoateHCID 12069039(E)-4-[2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethenyl]-benzoic acid

Produkt 1

HCID 19695066Ethyl (E)-4-[-2-(5,6,7,8-tetrahydro-5,5-dimethyl-8-(1,3-dithian-2-yl)naphthalen-2-yl)ethenyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

To a cold solution (0 ° C.) of 140 mg (0.40 mmol) of ethyl (E)4-[2-(5,5-dimethyl-5,6,-dihydro-naphthalen-8(7H)-one-2-yl)ethenyl]-benzoate (Compound A2), in 6.0 mL of methylene chloride was added dropwise 130 mg (0.12 mL, 1.2 mmol) of 1,3-propanedithiol and 0.17g (0.15 mL, 102 mmol) of borontrifluoride diethyl etherate. The reaction stirred between 0 ° C. and room temperature for 4 h. The mixture was diluted with aqueous sat. potassium carbonate, and extracted with ether (2x). The organic phase was washed with brine, dried over MgSO4 and then concentrated in vacuo. The crude product was purified by flash chromatography (silica, 10 % ethyl acetate in hexane) to afford the title compound as a solid.

Aufarbeitung

  1. extractionextracted with ether (2x)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography (silica, 10 % ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-097786b3e7694a0ab40c4631aa6404c4
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06117987

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