Boron trifluoride etherate → methyl 4-((1R,2R)-2-hydroxycyclopentyloxy)-3-methoxybenzoate

HRID 2204176Notes

Reaction equation

HRID 2204176 reaction equation
[CH:1]12[O:6][CH:5]1[CH2:4][CH2:3][CH2:2]2.[OH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=1[O:18][CH3:19].B(F)(F)F.CCOCC>C1C=CC=CC=1.C(OCC)(=O)C>[OH:6][C@@H:1]1[CH2:2][CH2:3][CH2:4][C@H:5]1[O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=1[O:18][CH3:19]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 92446-Oxabicyclo[3.1.0]hexaneHCID 19844Methyl Vanillate

Product 1

HCID 58550939methyl 4-((1R,2R)-2-hydroxycyclopentyloxy)-3-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Oxabicyclo[3.1.0]hexane (2.43 g, 2.50 mL, 28.9 mmol) was added dropwise to a stirred solution of methyl 4-hydroxy-3-methoxy-benzoate (5.26 g, 28.9 mmol) and BF3.OEt2 (410 mg, 369 μL, 2.89 mmol) in benzene (10 mL) at ambient temperature. The mixture was stirred at room temperature overnight before it was diluted with ethyl acetate and was washed with 1N NaOH. The organic layer was dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography eluting with 0-100% EtOAc in hexanes to give methyl 4-((1R,2R)-2-hydroxycyclopentyloxy)-3-methoxybenzoate. ESI-MS m/z talc. 266.1, found 267.1 (M+1)+; Retention time: 1.16 minutes (3 min run).

Workup

  1. washwas washed with 1N NaOH
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with 0-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-71078532ff934faca993fccd692004ea
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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