Acetaldehyde → HCID 23443043、化合物

HRID 1839537ノート

反応式

HRID 1839537 の反応式
C(NC(C)C)(C)C.[C:8]12([CH3:18])[C:15]([CH3:17])([CH3:16])[CH:12]([CH2:13][CH2:14]1)[CH2:11][C:9]2=[O:10].[CH:19](=[O:21])[CH3:20].C(=O)([O-])O.[Na+]>C1COCC1.CCCCCC>[OH:21][CH:19]([CH:11]1[CH:12]2[C:15]([CH3:17])([CH3:16])[C:8]([CH3:18])([CH2:14][CH2:13]2)[C:9]1=[O:10])[CH3:20].[OH:21][CH:19]([CH:11]1[CH:12]2[C:15]([CH3:17])([CH3:16])[C:8]([CH3:18])([CH2:14][CH2:13]2)[CH:9]1[OH:10])[CH3:20]

参加物

8

反応物 4

HCID 177AcetaldehydeHCID 2537CamphorHCID 7912DiisopropylamineHCID 516892Sodium Bicarbonate

生成物 2

HCID 147599003-(1-Hydroxyethyl)-camphorHCID 23443043HCID 23443043、化合物収率 126.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

実験手順

2.50 ml of 2.5M n-butylithium hexane solution was added dropwise to a tetrahydrofuran solution comprising 4 ml THF and 1.00 ml diisopropylamine at −78° C. and the mixture was stirred for 15 minutes. Then, a solution comprising 4 ml THF with 0.91 g camphor dissolved therein was added dropwise to the above solution at −78° C., then, 0.27 g of acetaldehyde was further added and the mixture was stirred for 15 minutes. Thus, 3-(1-hydroxyethyl)-camphor was synthesized. This reaction solution was admixed with 50 ml of saturated sodium hydrogen carbonate aqueous solution and restored to room temperature. The reaction product was extracted with diethylether. 5 ml of the above 3-(1-hydroxyethyl)-camphor diethylether solution was gradually added dropwise to 10 ml of a diethylether solution comprising 10 ml diethylether and 0.11 g lithium aluminum hydride and the mixture was stirred at room temperature for 30 minutes. 0.5 ml of water and 0.5 ml of 2N-NaOH were added to the reaction solution to separate the solids out. The separated-out solids were filtered off and the solvent was removed under vacuum. The residue was purified by means of silica gel column chromatography (eluent: hexane/ethylacetate=7/3) and 0.75 g of 3-(1-hydroxyethyl)-borneol was obtained (yield: 95%).

後処理

  1. customat −78° C.
  2. dissolutiondissolved
  3. additiontherein was added dropwise to the above solution at −78° C.
  4. stirringthe mixture was stirred for 15 minutes
  5. customrestored to room temperature
  6. extractionThe reaction product was extracted with diethylether
  7. addition5 ml of the above 3-(1-hydroxyethyl)-camphor diethylether solution was gradually added dropwise to 10 ml of a diethylether solution
  8. stirringthe mixture was stirred at room temperature for 30 minutes
  9. addition0.5 ml of water and 0.5 ml of 2N-NaOH were added to the reaction solution
  10. customto separate the solids out
  11. filtrationThe separated-out solids were filtered off
  12. customthe solvent was removed under vacuum
  13. customThe residue was purified by means of silica gel column chromatography (eluent: hexane/ethylacetate=7/3)

出典と根拠

ORDレコード
ord-4a5e9505dfb14947bc0ea8a87b8d626f
出典データセット
uspto-grants-2004_01
特許番号
US06677384B1

反応ノート

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