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

HRID 1007970ノート

反応式

HRID 1007970 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 88.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a round bottomed flask was added (±)-{4-[2,4-bis(methoxymethoxy)phenyl]cyclohexylidene}acetonitrile (141 mg) and methanol (5 ml). The reaction mixture was stirred, the solution was heated under 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 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 (90 mg, 88%) as a white solid. 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), 6.27 (1H, dd), 6.32 (1H, d), 6.80 (1H, d).

後処理

  1. temperaturethe solution was heated
  2. additionwas added slowly
  3. temperatureHeating
  4. customThe reaction mixture was partitioned between ethyl acetate (30 ml) and water (10 ml)
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×15 ml)
  6. washthe combined organic layers washed with brine (20 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. 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-dfbea31e998a43a782709803a9721a5b
出典データセット
uspto-grants-2004_09
特許番号
US06797731B2

反応ノート

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