Water → HCID 178501147, 화합물

HRID 131283노트

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HRID 131283 반응식
[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

참가 물질

5

반응물 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 178501162HCID 178501162, 화합물

생성물 1

HCID 178501147HCID 178501147, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-10 °C

실험 절차

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]+

후처리

  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)

출처 및 근거

ORD 기록
ord-a19c119db8ad4006908ea62855d6c1c4
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384952B2

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