Citric Acid → 8-(2-(Benzyloxy)ethyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

HRID 39707

反応式

HRID 39707 の反応式
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[O:19]1[C:23]2([CH2:28][CH2:27][CH:26]([C:29]#[N:30])[CH2:25][CH2:24]2)[O:22][CH2:21][CH2:20]1.Br[CH2:32][CH2:33][O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)(=O)C.O1CCCC1>[CH2:35]([O:34][CH2:33][CH2:32][C:26]1([C:29]#[N:30])[CH2:27][CH2:28][C:23]2([O:22][CH2:21][CH2:20][O:19]2)[CH2:24][CH2:25]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

8

反応物 5

HCID 311Citric AcidHCID 7912DiisopropylamineHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 111164331,4-Dioxaspiro[4.5]decane-8-carbonitrileHCID 178418244HCID 178418244、化合物

生成物 1

HCID 675392928-(2-(Benzyloxy)ethyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To 8 mL of a tetrahydrofuran solution containing 0.94 mL of diisopropylamine, 4.5 mL of 1.6 mol/L butyllithium/hexane was added dropwise at −78° C., the mixture was stirred at the same temperature for 1 hour, and then thereto was added dropwise 7 mL of a tetrahydrofuran solution containing 0.60 g of 1,4-dioxaspiro[4.5]decane-8-carbonitrile. After stirring at −78° C. for 1 hour, the mixture was added dropwise with 0.85 mL of benzyl 2-bromoethyl ether, and further stirred for 1 hour. The temperature of the reaction mixture was increased to room temperature, and then a 10% aqueous citric acid solution and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and then dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=6:1] to obtain 1.1 g of a colorless oily substance, 8-(2-(benzyloxy)ethyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile.

後処理

  1. additionwas added dropwise at −78° C.
  2. stirringAfter stirring at −78° C. for 1 hour
  3. stirringfurther stirred for 1 hour
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=6:1]

出典と根拠

ORDレコード
ord-d5b6baf518b046cfb7ba5027910852b9
出典データセット
uspto-grants-2013_09
特許番号
US08524738B2

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