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Methanol → 3-(3-{2-[3-(3-Hydroxy-2,2-dimethylpropyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethylpropan-1-ol

HRID 873283
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 873283
[Li+].[BH4-].[CH3:3][OH:4].C(OC(=O)C(C)(C)C[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30]([C:33](OCC)=[O:34])([CH3:32])[CH3:31])[CH:24]=2)[S:22][CH2:21][CH2:20][CH2:19][S:18]1)C.[NH4+].[Cl-]>C(Cl)Cl>[OH:34][CH2:33][C:30]([CH3:31])([CH3:32])[CH2:29][C:25]1[CH:24]=[C:23]([C:17]2([C:12]3[CH:11]=[C:16]([CH2:11][C:12]([CH3:17])([CH3:13])[CH2:3][OH:4])[CH:15]=[CH:14][CH:13]=3)[S:18][CH2:19][CH2:20][CH2:21][S:22]2)[CH:28]=[CH:27][CH:26]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 867297993-{(2-[3-(2-Ethoxycarbonyl-2-methylpropyl}-phenyl]-[1,3]dithian-2-yl)-phenyl)-2,2-dimethylpropionic acid ethyl ester

Produkt 1

HCID 114649623-(3-{2-[3-(3-Hydroxy-2,2-dimethylpropyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethylpropan-1-ol
Ausbeute 170,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of LiBH4 (0.78 g, 35.8 mmol) in CH2Cl2 (55 mL) was added methanol (1.04 g, 32.5 mmol) at room temperature. After the addition of 229 (6.5 g, 12.3 mmol), the reaction mixture was heated to reflux for 6 h. After cooling to room temperature, saturated aqueous NH4Cl solution (20 mL) and CH2Cl2 (15 mL) were added and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to afford 230 (4.66 g, 85%) as an oil. 1H NMR (CDCl3): δ 7.42 (s br., 2H), 7.17 (m, 4H), 6.97 (m, 2H), 3.63 (s, 4H), 3.16 (s, 4H), 2.69 (m, 2H), 2.47 (m, 4H), 1.88 (m, 2H), 0.75 (s, 12H). 13C NMR (CDCl3): δ 142.39, 139.18, 131.69, 129.88, 128.05, 127.01, 71.12, 44.89, 43.74, 36.70, 29.63, 24.22.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×10 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8bcb63814f6f4a59abd05bb6cc810103
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08975300B2

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