Triethylamine → 3-(Diethoxymethyl)phenethyl methanesulfonate

HRID 471011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471011
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:8][CH:9]([O:19][CH2:20][CH3:21])[C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][OH:18])[CH:13]=[CH:14][CH:15]=1)[CH3:7].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:18][CH2:17][CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH:9]([O:8][CH2:6][CH3:7])[O:19][CH2:20][CH3:21])[CH:11]=1)(=[O:4])=[O:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 579893032-(3-(Diethoxymethyl)phenyl)ethanol

Produkt 1

HCID 579889463-(Diethoxymethyl)phenethyl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Methanesulfonyl chloride (0.18 g) in dichloromethane (0.2 mL) was added to a stirred solution of 2-(3-(diethoxymethyl)phenyl)ethanol (example 20, step c) (0.23 g) and triethylamine (0.429 mL) in dichloromethane (2.5 mL) cooled in an ice bath. After 1 h, the reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The ethyl acetate layer was washed with saturated sodium bicarbonate solution and brine, dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound as a gum. Yield 0.28 g.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. washThe ethyl acetate layer was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-89a08a0dc47e45da9cc190d2975334d5
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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