Cyclohexanemethanol → HCID 66847338, compound

HRID 1401129Notes

Reaction equation

HRID 1401129 reaction equation
[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1.O>[CH:1]1([CH2:7][O:8][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 7507CyclohexanemethanolHCID 13831TributylphosphineHCID 24522Ethyl 3-hydroxybenzoateHCID 730421,1'-(Azodicarbonyl)dipiperidine

Product 1

HCID 66847338HCID 66847338, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Cyclohexyl methanol (2.0 g, 17.5 mmol), ethyl 3-hydroxybenzoate (2.6 g, 15.8 mmol), tri-n-butyl phosphin (5.3 g, 26 mmol), and ADDP (6.6 g, 26 mmol) were dissolved in dry THF (100 ml) and stirred overnight at 20° C. under N2. Water (100 ml) is added, and the resulting solution is extracted with DCM (3×100 ml). The combined organic layers were washed with water (100 ml), dried (MgSO4) and evaporated. The crude mixture was purified by preparative HPLC to give 1.8 g of the title compound. LC-MS (m/z): 264 (M+2).

Workup

  1. extractionthe resulting solution is extracted with DCM (3×100 ml)
  2. washThe combined organic layers were washed with water (100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-e7a6e504066f44d8a688a9df7ddc5978
Source dataset
uspto-grants-2014_12
Patent number
US08907096B2

Reaction notes

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