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Triethylamine → 3-(2,4-Dihydroxyphenyl)-acrylic acid 1,5-dimethyl-1-vinyl-hex-4-enyl ester

HRID 2220805
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2220805
NC(C)C[C:4]([CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH:9]=[CH:8][CH:7]1[CH3:14])=O.C(N(CC)CC)C.[OH:23][C:24]1[CH:29]=[C:28]([OH:30])[CH:27]=[CH:26][C:25]=1[CH:31]=[CH:32][C:33]([OH:35])=[O:34].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.CN(C=O)C>[CH3:14][C:7]([O:34][C:33](=[O:35])[CH:32]=[CH:31][C:25]1[CH:26]=[CH:27][C:28]([OH:30])=[CH:29][C:24]=1[OH:23])([CH:6]=[CH2:4])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 33594933-(2,4-dihydroxyphenyl)prop-2-enoic AcidHCID 219471233-Amino-1-(2,6,6-trimethyl-cyclohex-3-enyl)-butan-1-one

Produkt 1

HCID 669332403-(2,4-Dihydroxyphenyl)-acrylic acid 1,5-dimethyl-1-vinyl-hex-4-enyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-1-(2,6,6-trimethyl-cyclohex-3-enyl)-butan-1-one (2.38, 11.3 mmol, 10) and triethylamine (2.30 g, 22.6 mmol) in anhydrous THF (150 mL) stirred for 5 min at 22° C. is added 3-(2,4-dihydroxyphenyl)-acrylic acid (2.04 g, 11.3 mmol). To this heterogeneous solution is added BOP Reagent (5.00 g, 11.3 mmol; Aldrich #22,608-4) in DMF (10 mL), and the subsequent homogeneous reaction mixture is stirred for 1 h. The reaction mixture is partitioned between ether (200 mL) and water (400 mL); the organic layer is removed and washed with ether (200 mL). The combined organic layers are washed sequentially with saturated sodium bicarbonate solution (200 mL) and brine (200 mL). The organic layer is dried over anhydrous magnesium sulfate, vacuum filtered and concentrated to give 3-(2,4-dihydroxy-phenyl)-acrylic acid 1,5-dimethyl-1-vinyl-hex-4-enyl ester as an oil that is purified by flash chromatography to give 11 as a colorless solid.

Aufarbeitung

  1. customThe reaction mixture is partitioned between ether (200 mL) and water (400 mL)
  2. customthe organic layer is removed
  3. washwashed with ether (200 mL)
  4. washThe combined organic layers are washed sequentially with saturated sodium bicarbonate solution (200 mL) and brine (200 mL)
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate, vacuum
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f5844642a03442089b5075c8e9f868d9
Quelldatensatz
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07368415B2

Notizen zur Reaktion

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