Oxalic Acid → HCID 131724378、化合物

HRID 49410ノート

反応式

HRID 49410 の反応式
CO[C:3]1[CH2:4][C:5]2[CH2:6][C@@H:7]([CH3:24])[C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@:9]23[CH2:23][C@@H:10]2[CH2:11][C@H:12]1[CH2:21]O.C(O)(=O)[C:26](O)=[O:27].C(=O)([O-])[OH:32].[Na+]>CO.O1CCCC1.O>[OH:27][CH2:26][CH2:21][C@@H:12]1[CH2:11][C@H:10]2[CH2:23][C@@:9]32[C@H:8]2[C@H:17]([CH2:16][CH2:15][C@:13]13[CH3:14])[C:18]1[CH2:19][CH2:20][C:3](=[O:32])[CH2:4][C:5]=1[CH2:6][C@H:7]2[CH3:24]

参加物

7

反応物 3

HCID 971Oxalic AcidHCID 516892Sodium BicarbonateHCID 69625019(7alpha,14beta,15beta,17alpha)-3-Methoxy-7-methyl-14,15-methyleneestra-2,5(10)-diene-17-methanol

生成物 1

HCID 131724378HCID 131724378、化合物

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (7α,14β,15β,17α)-3-methoxy-7-methyl-14,15-methyleneestra-2,5(10)-diene-17-methanol (Example 1, step vi; 7.38 g) in a mixture of methanol (68 ml) and tetrahydrofuran (48 ml) was treated with a solution of oxalic acid (2.38 g) in water (40 ml). After 1 h stirring at room temperature, the reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate and the product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (7α,14β,15β,17α)-17-(hydroxyethyl)-7-methyl-14,15-methyleneestr-5(10)-en-3-one (4.27 g). 1H NMR (CDCl3) δ3.69 (m, 1H), 3.51 (t, 1H, J=9.0 Hz), 2.72 (bs, 2H), 2.46 (bs, 2H), 1.04 (s, 3H), 0.69 (d, 3H, J=7.1 Hz), 0.48(dd, 1H, J=8.3 and 5.1 Hz), 0.27 (dd, 1H, J=5.1 and 3.1 Hz).

後処理

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d3ce938e8ba948cdb819560530d83ab7
出典データセット
uspto-grants-2004_03
特許番号
US06706700B2

反応ノート

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