Diethyl Ether → (+/-)-cis-4-(Cyanomethyl)-1,5dioxaspiro[5.5]undecane-2-acetic acid

HRID 360021

반응식

HRID 360021 반응식
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[O:14]=[CH:15][CH2:16][C@H:17]1[O:22][C:21]2([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[O:20][C@@H:19]([CH2:28][C:29]#[N:30])[CH2:18]1.C(OCC)C>CC(C)=O>[C:29]([CH2:28][C@H:19]1[O:20][C:21]2([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[O:22][C@@H:17]([CH2:16][C:15]([OH:3])=[O:14])[CH2:18]1)#[N:30]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 86744692(+/-)-cis-4-(2-Oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrileHCID 131709961Jones' reagent

생성물 1

HCID 15045140(+/-)-cis-4-(Cyanomethyl)-1,5dioxaspiro[5.5]undecane-2-acetic acid

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Jones reagent (chromium trioxide-sulfuric acid-water), 4.4 mL (8.85 mmol), is added dropwise to a 0° C. solution of (±)-cis-4-(2-oxoethyl)-1,5-dioxaspiro[5.5]undecane-2-acetonitrile, 3.62 g (12.6 mmol), dissolved in 30 mL of acetone until the orange color is not discharged. After stirring a further 15 minutes, the mixture is poured into 300 mL of diethyl ether and washed with brine until the aqueous washes are colorless. The diethyl ether layer is dried (magnesium sulfate), filtered, and concentrated to provide 3.65 g of (±)-cis-4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetic acid as a yellow solid.

후처리

  1. washwashed with brine until the aqueous washes
  2. dry with materialThe diethyl ether layer is dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c3cb9265daaa465c8f58859c12fa6613
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05003080

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