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Acetic Acid → 3,4-Di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbaldehyde

HRID 372126
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 372126
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH:12]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:11][CH:10]([C:20]#N)[CH:9]1[CH2:22][CH2:23][CH:24]([O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[H-].C([Al+]CC(C)C)C(C)C.C(O)(=[O:49])C>C(OCC)C.C1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH:12]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:11][CH:10]([CH:20]=[O:49])[CH:9]1[CH2:22][CH2:23][CH:24]([O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 21225700DiisobutylaluminumhydrideHCID 86732993HCID 86732993, Verbindung

Produkt 1

HCID 544198253,4-Di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel
HCID 3283
Diethyl Ether
Lösungsmittel

Versuchsvorschrift

To a vigorously stirred solution of crude 3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)-octyl]cyclopentane carbonitrile (7.9 g.) [prepared as described in (1) above] in dry diethyl ether (50 ml.) was added a solution of di-isobutylaluminium hydride (4.6 g.) in dry benzene (20 ml.) at 3°-7° C. The mixture was stirredat room temperature for 15 minutes and then added with stirring to aqueous 2N acetic acid solution (75 ml.) at below 15° C. The organic phase was separated, and the aqueous layer extracted with diethyl ether. The combined organic phases were washed with aqueous sodium bicarbonate and with water, dried over magnesium sulphate, and the solvents removed in vacuo to give crude 3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbaldehyde (7.7 g.), which was used as starting material in the following preparation (n) of ethyl 7-{3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}hepta-2,4,6-trienoate without further purification.

Aufarbeitung

  1. additionadded
  2. customThe organic phase was separated
  3. extractionthe aqueous layer extracted with diethyl ether
  4. washThe combined organic phases were washed with aqueous sodium bicarbonate and with water
  5. dry with materialdried over magnesium sulphate
  6. customthe solvents removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d504917b7f874dc7b27fefa8a7373ebe
Quelldatensatz
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04088821

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