Hydrochloric Acid → [4-(2,4-Dihydroxyphenyl)cyclohexylidene]acetonitrile

HRID 585669ノート

反応式

HRID 585669 の反応式
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][C:18](=[CH:21][C:22]#[N:23])[CH2:17][CH2:16]1.Cl.C(=O)(O)[O-].[Na+]>CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:16][CH2:17][C:18](=[CH:21][C:22]#[N:23])[CH2:19][CH2:20]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 22337767{4-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylidene}acetonitrile

生成物 1

HCID 9964617[4-(2,4-Dihydroxyphenyl)cyclohexylidene]acetonitrile収率 88%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a round bottomed flask equipped with magnetic stirrer was added (±)-{4-[2,4-bis(methoxymethoxy)phenyl]cyclohexylidene}acetonitrile (141 mg, 0.45 mmol) and methanol (5 ml). The reaction mixture was stirred, the solution was heated to reflux temperature and aqueous hydrochloric acid (5 ml, 1.0M) was added slowly. Heating was continued for 1 hr and the reaction mixture was allowed to cool to room temperature prior to the addition of saturated aqueous sodium bicarbonate solution (12 ml). The reaction mixture was then partitioned between ethyl acetate (30 ml) and water (10 ml). The aqueous layer was extracted with ethyl acetate (3×15 ml) and the combined organic layers washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:1, v/v) to afford the title compound as a white solid (90 mg, 88%). m/z (ES−) 228 (M−H+); δH(CD3OD) 1.56-1.68 (2H, m), 2.02-2.14 (2H, m), 2.33-2.48 (2H, m), 2.57 (1H, m), 3.01 (1H, m), 3.14 (1H, m), 5.31 (1H, s), 6.26 and 6.28 (1H, d), 6.32 (1H, d), 6.80 (1H, d).

後処理

  1. customTo a round bottomed flask equipped with magnetic stirrer
  2. temperaturethe solution was heated
  3. additionwas added slowly
  4. temperatureHeating
  5. customThe reaction mixture was then partitioned between ethyl acetate (30 ml) and water (10 ml)
  6. extractionThe aqueous layer was extracted with ethyl acetate (3×15 ml)
  7. washthe combined organic layers washed with brine (20 ml)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:1

出典と根拠

ORDレコード
ord-5c8d7eec7e174f0e931703f6b7fbfed2
出典データセット
uspto-grants-2005_08
特許番号
US06933319B2

反応ノート

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