Triethylamine → [1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methyl methanesulfonate

HRID 906437

Reaktionsgleichung

Reaktionsgleichung von HRID 906437
[Si:1]([O:8][CH2:9][C:10]1([CH2:13][OH:14])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl.O>[CH3:22][S:23]([O:14][CH2:13][C:10]1([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:11][CH2:12]1)(=[O:25])=[O:24]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59000904(1-(((tert-Butyldimethylsilyl)oxy)methyl)cyclopropyl)methanol

Produkt 1

HCID 59000927[1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methyl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of [1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanol (Example 34c, 5.37 g) dissolved in DCM (20 mL) was treated with triethylamine (6.92 mL) at 0° C. before adding methanesulfonyl chloride (2.321 mL) under nitrogen. The resulting mixture was stirred at 0° C. for 30 min. The reaction mixture was diluted with water (100 mL), and extracted with DCM (250 mL). The organics were dried (MgSO4), filtered and evaporated. The crude product was purified (SiO2 chromatography, elution 50% isohexane in diethyl ether). Pure fractions were evaporated to dryness to afford the subtitle compound (5.37 g) as an oil.

Aufarbeitung

  1. extractionextracted with DCM (250 mL)
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified
  6. wash(SiO2 chromatography, elution 50% isohexane in diethyl ether)
  7. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-2be7449450db4b7bb51f95b6aae5ad43
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012980B2

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