Hydrochloric Acid → [6-(Hydroxymethyl)-3-cyclohexenyl]-N-octadecylformamide

HRID 566419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566419
[CH2:1]([N:19]1[C:27](=O)[CH:26]2C(C[CH:23]=[CH:24][CH2:25]2)[C:20]1=[O:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C[CH:31]([OH:33])[CH3:32].[BH4-].[Na+].Cl>O>[OH:33][CH2:31][CH:32]1[CH:27]([N:19]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:20]=[O:29])[CH2:26][CH:25]=[CH:24][CH2:23]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 212661442-Octadecyl-4,7,3a,7a-tetrahydroisoindole-1,3-dione

Produkt 1

HCID 86756229[6-(Hydroxymethyl)-3-cyclohexenyl]-N-octadecylformamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2-Octadecyl-4,7,3a,7a-tetrahydroisoindole-1,3-dione (5.00 g) was suspended into a mixture of 2-propanol (90 ml) and water (15 ml) and then sodium borohydride (2.34 g) was added thereto. After being stirred for 46 hours at room temperature, the reaction mixture was acidified with dilute hydrochloric acid and then concentrated. The residue was, with chloroform added thereto, washed with dilute hydrochloric acid, water and saturated sodium hydrogencarbonate aqueous solution successively, dried over sodium sulfate anhydride, and concentrated. The residue was purified by silica gel column chromatography (silica gel 80 g, chloroform:methanol=50:1-10:1), thereby yielding the entitled compound (4.32 g) as white crystals.

Aufarbeitung

  1. concentrationconcentrated
  2. additionadded
  3. washwashed with dilute hydrochloric acid, water and saturated sodium hydrogencarbonate aqueous solution successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (silica gel 80 g, chloroform:methanol=50:1-10:1)

Quellen und Nachweise

ORD-Eintrag
ord-a05458d6b26d497282ef231344e0aa16
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06174885B1

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