Sodium Hydroxide → 6-Cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

HRID 356485ノート

反応式

HRID 356485 の反応式
C[O:2][C:3](=[O:25])[CH2:4][C:5](=[O:24])[CH2:6][C:7]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)(O)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[OH-].[Na+]>O1CCCC1>[CH:18]1([C:7]2([CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)[O:25][C:3](=[O:2])[CH:4]=[C:5]([OH:24])[CH2:6]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 543367345-Cyclohexyl-5-hydroxy-7-(4-hydroxy-phenyl)-3-oxo-heptanoic acid methyl ester

生成物 1

HCID 547203146-Cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Crude 5-cyclohexyl-5-hydroxy-7-(4-hydroxy-phenyl)-3-oxo-heptanoic acid methyl ester (prepared in the previous paragraph) was dissolved in tetrahydrofuran (100 mL) and treated with 0.2N NaOH (900 mL) as described in General Method 7. The reaction was stirred for 3 hours at room temperature and then worked up as usual. The organic extracts obtained were combined, dried (MgSO4) and concentrated. Purification was accomplished by flash chromatography using CH2Cl2 :MeOH (99:1 to 98:2) to give the desired product as a solid, m.p. 52°-58° C. 1H NMR (CDCl3) δ 1.0-1.9 (m, 12 H), 1.9-2.1 (m, 1 H), 2.5-2.7 (m, 3 H), 2.8 (d, 1 H), 3.4 (s, 2 H), 6.75 (d, 2 H), 7.05 (d, 2 H).

後処理

  1. customThe organic extracts obtained
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification

出典と根拠

ORDレコード
ord-f8d58b4912c547e195808d4fabf9e33d
出典データセット
uspto-grants-1998_11
特許番号
US05834506

反応ノート

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