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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 661160
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 661160
[Li+].[BH4-].CO.C([O:7][C:8](=O)[C:9]([CH3:39])([CH3:38])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30]([C:33](OCC)=[O:34])([CH3:32])[CH3:31])[CH:24]=3)[S:22][CH2:21][CH2:20][CH2:19][S:18]2)[CH:12]=1)C.[NH4+].[Cl-]>C(Cl)Cl>[OH:7][CH2:8][C:9]([CH3:39])([CH3:38])[CH2:10][C:11]1[CH:12]=[C:13]([C:17]2([C:23]3[CH:24]=[C:25]([CH2:29][C:30]([CH3:32])([CH3:31])[CH2:33][OH:34])[CH:26]=[CH:27][CH:28]=3)[S:18][CH2:19][CH2:20][CH2:21][S:22]2)[CH:14]=[CH:15][CH:16]=1
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Komponenten

6

Edukt 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 113185153-(3-{2-[3-(2-Ethoxycarbonyl-2-methyl-propyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethyl-propanoic 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 85,2 %

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-d931433472be4ce3a63d31eccef35081
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08084498B2

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