Water → HCID 178501147, compound

HRID 131283Notes

Reaction equation

HRID 131283 reaction equation
[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

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 178501162HCID 178501162, compound

Product 1

HCID 178501147HCID 178501147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

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]+

Workup

  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)

Sources & evidence

ORD record
ord-a19c119db8ad4006908ea62855d6c1c4
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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