4-[3-Methoxy-4-(methoxymethoxy)phenyl]but-3-en-2-one → 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one

HRID 77672

反応式

HRID 77672 の反応式
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=1[O:16][CH3:17]>CO.Cl>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=1[O:16][CH3:17]

参加物

4

反応物 1

HCID 695016824-[3-Methoxy-4-(methoxymethoxy)phenyl]but-3-en-2-one

生成物 1

HCID 141214-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one収率 74%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

1-(4-Methoxymethyloxy-3-methoxyphenyl)-1-buten-3-one (35j, 0.40 g, 1.7 mmol) was dissolved in methanol (40 ml) and stirred for 15 min at 50° C. Hydrochloric acid (3 drops) was added and the mixture stirred for 18 hr at 65° C. The methanol was evaporated and the resulting residue extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was chromatographed on silica gel with ethyl acetate/hexane to give 0.24 g (74%) of an orange-yellow solid: mp 120-122° C. [expected mp 128-129° C.]; 1H NMR δ 2.34 (s, 3H), 3.91 (s, 3H), 5.98 (s, 1H), 6.56 (d, 1H, J=16.1 Hz), 6.91 (d, 1H, J=8.2 Hz), 7.04 (m, 2H), 7.43 (d, 1H, J=16.3 Hz); 13C NMR: δ 27.3, 56.0, 109.3, 114.8, 123.4, 124.9, 126.9, 143.6, 146.8, 148.2, 198.2.

後処理

  1. stirringthe mixture stirred for 18 hr at 65° C
  2. customThe methanol was evaporated
  3. extractionthe resulting residue extracted into ethyl acetate
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a solid
  9. customThe crude solid was chromatographed on silica gel with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-5718adf006a54864bb31c397ba939ec5
出典データセット
uspto-grants-2014_09
特許番号
US08841326B2

関連ノート

読み込み中…