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Tetrabutylammonium Fluoride → Methyl [4-(2-chlorophenyl)-2-(4-hydroxyphenyl)thien-3-yl]acetate

HRID 2373705
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2373705
[Si](OC1C=CC(B(O)O)=CC=1)(C(C)(C)C)(C)C.BrC1C(CC(OC)=O)=C(C2C=CC(O[Si](C(C)(C)C)(C)C)=CC=2)SC=1.ClC1C=CC=CC=1B(O)O.[Si]([O:60][C:61]1[CH:66]=[CH:65][C:64]([C:67]2[S:68][CH:69]=[C:70]([C:77]3[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=3[Cl:83])[C:71]=2[CH2:72][C:73]([O:75][CH3:76])=[O:74])=[CH:63][CH:62]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:83][C:78]1[CH:79]=[CH:80][CH:81]=[CH:82][C:77]=1[C:70]1[C:71]([CH2:72][C:73]([O:75][CH3:76])=[O:74])=[C:67]([C:64]2[CH:65]=[CH:66][C:61]([OH:60])=[CH:62][CH:63]=2)[S:68][CH:69]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 2724141Tetrabutylammonium FluorideHCID 27343222-Chlorophenylboronic acidHCID 111078154-(tert-Butyldimethylsilyloxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 86607177Methyl [4-bromo-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)thien-3-yl]acetateHCID 86607178Methyl [2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-(2-chlorophenyl)thien-3-yl]acetate
2×

Produkt 1

HCID 86607176Methyl [4-(2-chlorophenyl)-2-(4-hydroxyphenyl)thien-3-yl]acetateAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

This compound was prepared in a fashion similar to Example 1 with the following modifications: 4(t-Butyldimethylsilyloxy)phenylboronic acid (2.53 g, 10.0 mmol) was used in Step 5 to synthesize methyl [4-bromo-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)thien-3-yl]acetate (2.71 g). This material was reacted as in Example 1 Step 6 with 2-chlorophenylboronic acid (1.93 g, 12.31 mmol) to synthesize methyl [2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-(2-chlorophenyl)thien-3-yl]acetate (2.12 g). Methyl [2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-(2-chlorophenyl)thien-3-yl]acetate (2.00 g, 4.22 mmol) was dissolved in THF and a solution of tetrabutylammonium fluoride in THF (4.65 mL, 1 M, 4.65 mmol) was added dropwise. The solution was heated to 60° C. and stirred for 3 h. The solvent was removed and the mixture was partitioned between EtOAc and 1N HCl. The EtOAc was washed with H2O, dried (MgSO4), and the solvent removed to yield methyl [4-(2-chlorophenyl)-2-(4-hydroxyphenyl)thien-3-yl]acetate (1.34 g) which was used without further purification.

Aufarbeitung

  1. customThis compound was prepared in a fashion similar to Example 1 with the following modifications
  2. customThe solvent was removed
  3. customthe mixture was partitioned between EtOAc and 1N HCl
  4. washThe EtOAc was washed with H2O
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-b33b184bf2e848e49950ee333a227880
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07459567B2

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