Boron trifluoride → ethyl (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexane-1-carboxylic acid

HRID 516817Notes

Reaction equation

HRID 516817 reaction equation
O[C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([O:10]CC)=[O:9].B(F)(F)F.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][O:29]/[C:30](=N/[H])/[C:31](Cl)(Cl)Cl)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]>C1(C)C=CC=CC=1>[CH2:4]([C@@:3]1([C:8]([OH:10])=[O:9])[CH2:2][CH2:7][CH2:6][CH2:31][C@H:30]1[O:29][CH2:28][CH2:27][C:21]1[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:19]([O:18][CH3:17])[CH:20]=1)[CH3:5]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 1268212trans-Ethyl 2-hydroxycyclohexanecarboxylateHCID 178506527HCID 178506527, compound

Product 1

HCID 86642594ethyl (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexane-1-carboxylic acidYield 110.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To ethyl (1R,2R)-2-hydroxycyclohexane-1-carboxylate (166) (1.7 g, 10 mmol) and BF3.EtO2 (280 mg, 250 μL, 2 mmol) in toluene (10 mL) was added dropwise a solution of 3,4-dimethoxyphenethoxy trichloroacetimidate (16) (3.26 g, 10 mmol) in toluene (15 mL). The resultant solution was stirred at ambient temperature for 2 hrs. The reaction mixture was then quenched with water (10 mL), the organic layer was collected, dried over anhydrous MgSO4 and concentrated in vacuo to give 3.71 g (quant. yield) of ethyl (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexane-1-carboxylic acid (167) which was used without further purification in the next step.

Workup

  1. customThe reaction mixture was then quenched with water (10 mL)
  2. customthe organic layer was collected
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-030d8ae0578e419895abb8cdb2964fe4
Source dataset
uspto-grants-2015_08
Patent number
US09115081B2

Reaction notes

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