Citric Acid → 8-Cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde

HRID 1948146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948146
[CH:1]1([CH2:4][C:5]2([C:15]#N)[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[O:17]1C2(CCC(C#N)CC2)OCC1.C1(CBr)CC1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH:1]1([CH2:4][C:5]2([CH:15]=[O:17])[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1

Komponenten

8

Edukt 6

HCID 311Citric AcidHCID 1140TolueneHCID 81503BromomethylcyclopropaneHCID 111164331,4-Dioxaspiro[4.5]decane-8-carbonitrileHCID 21225700DiisobutylaluminumhydrideHCID 670726938-(Cyclopropylmethyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Produkt 1

HCID 866563378-Cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 8-cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile, prepared from 1,4-dioxa-spiro[4.5]decane-8-carbonitrile and cyclopropylmethyl bromide in a similar fashion as described for 5, (3.00 g, 13.6 mmol) in tetrahydrofuran (40 mL) at −78° C. was added a 1M solution of diisobutylaluminium hydride in toluene (20.3 mL, 20.3 mmol, 1.5 eq.) and the reaction was allowed to warmed to 0° C. over a period of 3 h. The mixture was recooled to −78° C., neutralized by dropwise addition of a 10% aqueous citric acid solution and warmed to room temperature. The mixture was partitioned between methyl-tert.butyl ether and water, the aqueous phase extracted twice with methyl-tert.butyl ether and the combined organics were dried over magnesium sulphate, filtered and evaporated to give 8-cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde.

Aufarbeitung

  1. customwas recooled to −78° C.
  2. temperaturewarmed to room temperature
  3. customThe mixture was partitioned between methyl-tert.butyl ether and water
  4. extractionthe aqueous phase extracted twice with methyl-tert.butyl ether
  5. dry with materialthe combined organics were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-11b3c49a34aa44c298b233bf87529397
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399482B2

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