Acetyl chloride → Methyl 7-hydroxyhept-5-ynoate

HRID 1749232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749232
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+]>CO>[CH3:14][O:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]#[C:6][CH2:5][OH:4]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 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-1439f3b73b9d43bf87557976cd6044f5
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156810B2

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