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Triethylamine → HCID 69801944, Verbindung

HRID 585682
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 585682
C(N(CC)CC)C.[C:8](Cl)(=[O:11])[CH2:9][CH3:10].[Si:13]([O:20][C:21]1[CH:26]=[C:25]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH:24]=[CH:23][C:22]=1[CH:35]1[CH2:40][CH2:39][CH:38]([CH2:41][OH:42])[CH2:37][CH2:36]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CN(C)C1C=CN=CC=1.ClCCl>[C:8]([O:42][CH2:41][CH:38]1[CH2:37][CH2:36][CH:35]([C:22]2[CH:23]=[CH:24][C:25]([O:27][Si:28]([C:31]([CH3:33])([CH3:34])[CH3:32])([CH3:30])[CH3:29])=[CH:26][C:21]=2[O:20][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14])[CH2:40][CH2:39]1)(=[O:11])[CH2:9][CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 54354272HCID 54354272, Verbindung

Produkt 1

HCID 69801944HCID 69801944, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

4-Dimethylaminopyridine (catalytic amount), triethylamine (68 μl) and propionyl chloride (42 μl) were added to a stirred solution of [4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]methanol in anhydrous dichloromethane (3 ml) at room temperature under argon. After 16 hr, the reaction mixture was partitioned between water (10 ml) and ethyl acetate (20 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×20 ml). The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:19 v/v) to give the title compound as a yellow oil and a mixture of diastereoisomers (114 mg, 92%); δH (CDCl3) −0.04 (6H, s), 0.02 (6H, s), 0.96 (9H, s), 1.00 (9H, s), 1.08-1.18 (3H, m), 1.20-2.10 (9H, m), 2.24-2.40 (2H, m), 2.76-2.92 (1H, m), 3.94 (0.6H, d), 4.18 (0.4H, d), 6.26 (1H, m), 6.40 (1H, dd), 6.94-6.98 (1H, m).

Aufarbeitung

  1. customthe reaction mixture was partitioned between water (10 ml) and ethyl acetate (20 ml)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×20 ml)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:19 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-f9c005d5b03843bab17451750278852d
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06933319B2

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