Acetyl chloride → Methyl 7-hydroxyhept-5-ynoate

HRID 1814197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1814197
C([O:4][CH2:5][C:6]#[C:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=O)C.[C:14](Cl)(=O)C.C(=O)(O)[O-].[Na+].C([Si](C)(C)OCCCCC#CCO)(C)(C)C>CO>[CH3:14][O:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]#[C:6][CH2:5][OH:4]

Komponenten

6

Edukt 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 111725557-(tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-olHCID 219644197-Acetoxy-hept-5-ynoic acid

Produkt 1

HCID 11789443Methyl 7-hydroxyhept-5-ynoateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The crude acid 29 (6.333 g) was treated with a 1% solution of acetyl chloride in methanol (60 mL). After 16 h, sodium bicarbonate (1.966 g, 23.4 mmol) was added. The mixture was dried (MgSO4), filtered through celite and evaporated in vacuo. Purification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes) gave 7-Hydroxy-hept-5-ynoic acid methyl ester 30 (3.022 g, 19.3 mmol, 92% from 7-tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol 27).

Aufarbeitung

  1. dry with materialThe mixture was dried (MgSO4)
  2. filtrationfiltered through celite
  3. customevaporated in vacuo
  4. customPurification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-580b7f4c5c18410992e72e600c2e7852
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875787B2

Notizen zur Reaktion

Wird geladen…