Hydrochloric Acid → Diethyl 2-(2-benzyloxyethyl)-2-hydroxymethylmalonate

HRID 514632ノート

反応式

HRID 514632 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](=O)(O)[O-:23].[K+].C=O.Cl>C(#N)C>[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH2:22][OH:23])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 516893Potassium BicarbonateHCID 12549951Diethyl 2-(2-(benzyloxy)ethyl)malonate

生成物 1

HCID 67779176Diethyl 2-(2-benzyloxyethyl)-2-hydroxymethylmalonate収率 90.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
25 °C

実験手順

2.85 g (9.67 mmol equivalents) of diethyl 2-(2-benzyloxyethyl)malonate was dissolved in 20 mL of acetonitrile, 1.60 g (11.7 mmol equivalents) of potassium bicarbonate and 465 mg (11.7 mmol equivalents as formaldehyde) of paraformaldehyde were added thereto, and the mixture was stirred at room temperature (25° C.) overnight. After completion of the reaction, a 0.5 mol/L aqueous solution of hydrochloric acid was added dropwise to the reaction liquid, and the mixture was extracted three times with chloroform. The combined chloroform layers were dried with anhydrous magnesium sulfate and then concentrated under vacuum, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1) to give 2.78 g (8.76 mmol equivalents) of diethyl 2-(2-benzyloxyethyl)-2-hydroxymethylmalonate.

後処理

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted three times with chloroform
  3. dry with materialThe combined chloroform layers were dried with anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customthe obtained crude product
  6. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=4/1)

出典と根拠

ORDレコード
ord-9878d03cb2334e3bbe1aaa2241202dc5
出典データセット
uspto-grants-2015_08
特許番号
US09107964B2

反応ノート

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