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Dichloromethane → 3-Methoxy-3-(4-phenylphenyl)but-1-yl p-toluenesulfonate

HRID 1416515
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1416515
[CH3:1][O:2][C:3]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)([CH3:7])[CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.ClCCl>CC(C)=O.C(OCC)C>[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([O:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)[CH3:7])(=[O:35])=[O:34])=[CH:29][CH:28]=1
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Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 154045023-Methoxy-3-(4-phenylphenyl)butan-1-ol

Produkt 1

HCID 537569453-Methoxy-3-(4-phenylphenyl)but-1-yl p-toluenesulfonateAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180
Acetone
Lösungsmittel
2×
HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 3-methoxy-3-(4-phenylphenyl)butan-1-ol (2.04 g, 8.0 mmole, prepared in Example 8, Part B above) and triethylamine (1.51 g, 15 mmole) in acetone (10 mL) at 0° was added in one portion a solution of p-toluenesulfonyl chloride (2.85 g, 15 mmole) in acetone (4 mL). The resultant suspension was warmed to 20° C. and stirred at that temperature for 14 hours, then diluted with diethyl ether (40 mL). The resultant precipitate (triethylamine hydrochloride) was removed by filtration and the filtrate was evaporated to dryness to give a crude product, which was purified by column chromatography on silica gel, eluting with a 1:1 v/v hexanes:dichloromethane mixture to give the desired product (2.87 g, 87% yield) of colorless solid. Less pure fractions were combined to provide an additional 0.147 g of colorless solid which was crystallized from hexanes (10 mL), furnishing colorless fine matted needles weighing 0.070 g; melting point 69-70.5° C.

Aufarbeitung

  1. customThe resultant precipitate (triethylamine hydrochloride) was removed by filtration
  2. customthe filtrate was evaporated to dryness
  3. customto give a crude product, which
  4. customwas purified by column chromatography on silica gel
  5. washeluting with a 1:1 v/v hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7d148562c3674880a492b2e1512ee461
Quelldatensatz
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05914213

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