Hydrochloric Acid → (4S)-4-(2-tetrahydropyranyloxy)-1-nonanol

HRID 973341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 973341
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH:11]=[O:12].[BH4-].[Na+].Cl>COCCOCCOC>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][OH:12]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86735173(4S)-4-(2-tetrahydropyranyloxy)nonanal

Produkt 1

HCID 68122110(4S)-4-(2-tetrahydropyranyloxy)-1-nonanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Versuchsvorschrift

A solution of (4S)-4-(2-tetrahydropyranyloxy)-nonanal (43.5 g., 0.18 mole) in diglyme (125 ml.) is treated with sodium borohydride (3.8 g., 0.10 mole). The temperature rises to 45° with the resulting exothermic reaction. The solution is stirred 4 hours, acidified with concentrated hydrochloric acid, and concentrated on the rotary evaporator. Water is added to the residue and the oily product is taken up in ether; washed with water and brine and dried over sodium sulfate. Evaporation of the ether leaves (4S)-4-(2-tetrahydropyranyloxy)-1-nonanol as a colorless oil to be used in the next step without further purification.

Aufarbeitung

  1. customThe temperature rises to 45° with the resulting exothermic reaction
  2. concentrationconcentrated on the rotary evaporator
  3. additionWater is added to the residue
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the ether

Quellen und Nachweise

ORD-Eintrag
ord-f138a4ba4bf14b0aba1cefc2085fa96e
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04055597

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