Phosphorus oxychloride → 6-Ethynylspiro[4.5]dec-6-ene

HRID 1471371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1471371
[C:1]([C:3]1(O)[CH2:12][CH2:11][CH2:10][CH2:9][C:4]21[CH2:8][CH2:7][CH2:6][CH2:5]2)#[CH:2].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1]([C:3]1[C:4]2([CH2:9][CH2:10][CH2:11][CH:12]=1)[CH2:8][CH2:7][CH2:6][CH2:5]2)#[CH:2]

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 866475806-Ethynylspiro[4.5]decan-6-ol

Produkt 1

HCID 866475816-Ethynylspiro[4.5]dec-6-eneAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
87.5 °C

Versuchsvorschrift

At 20-27° C., a solution of 6-ethynylspiro[4.5]decan-6-ol (180 g, 1 mol) in pyridine (1 l) was treated dropwise with POCl3 (207 g, 2 mol). The resulting mixture was heated for 5.5 h heating at 85-90° C., poured into ice and extracted twice with pentane (800 and 300 ml). The combined organic phases were washed twice with water (500 ml), with a saturated aqueous solution of NaCl (300 ml), dried (MgSO4), and concentrated. Short-path Vigreux-distillation (8 mbar, head temperature: 85° C.) of the crude product (146 g) gave 6-ethynylspiro[4.5]dec-6-ene (122.9 g, 76%).

Aufarbeitung

  1. temperatureThe resulting mixture was heated for 5.5 h
  2. additionpoured into ice
  3. extractionextracted twice with pentane (800 and 300 ml)
  4. washThe combined organic phases were washed twice with water (500 ml), with a saturated aqueous solution of NaCl (300 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. distillationShort-path Vigreux-distillation (8 mbar, head temperature: 85° C.) of the crude product (146 g)

Quellen und Nachweise

ORD-Eintrag
ord-55372eea9f4e47cb86bea93b0edd0ea8
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012391B2

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