Water → HCID 178501147、化合物

HRID 131283ノート

反応式

HRID 131283 の反応式
[C@H:1]1([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5][C@H:4]([C:7]([O-])=[O:8])[CH2:3][CH2:2]1.O.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:8][CH2:7][C@H:4]1[CH2:3][CH2:2][C@H:1]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1

参加物

5

反応物 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 178501162HCID 178501162、化合物

生成物 1

HCID 178501147HCID 178501147、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

The compound obtained in Reference Example 85(2) (mono-methyl trans-cyclohexane-1,4-dicarboxylate, 14.3 g) is dissolved in tetrahydrofuran (78 mL) and 1.0M boran-tetrahydrofuran complex solution in tetrahydrofuran (100 mL) is added dropwise thereto at −50° C. under argon gas atmosphere over a period of 1 hour. The mixture is stirred at −10° C. for 1 hour. To the reaction mixture is added water (160 mL) and a saturated sodium hydrogencarbonate solution (160 mL) under ice-cooling and the mixture is extracted with ethyl acetate (×4). The extract is washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is purified by flash column chromatography on silica gel (Solvent; chloroform:methanol=20:1) to give methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (13.25 g, yield; quantitative) as an oil. MS (APCI) m/z; 173 [M+H]+

後処理

  1. extractionthe mixture is extracted with ethyl acetate (×4)
  2. washThe extract is washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash column chromatography on silica gel (Solvent; chloroform:methanol=20:1)

出典と根拠

ORDレコード
ord-a19c119db8ad4006908ea62855d6c1c4
出典データセット
uspto-grants-2008_06
特許番号
US07384952B2

反応ノート

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