Water → (S)-methyl 2-(6-((4'-(cyclopentyloxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 2280650Notes

Reaction equation

HRID 2280650 reaction equation
CS([O:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)(=O)=O.O[C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27]3[CH:40]=[CH:39][C:30]4[C@H:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:32][O:33][C:29]=4[CH:28]=3)[CH:20]=2)=[C:14]([CH3:41])[CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH:6]1([O:5][C:12]2[CH:13]=[C:14]([CH3:41])[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27]4[CH:40]=[CH:39][C:30]5[C@H:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:32][O:33][C:29]=5[CH:28]=4)[CH:20]=3)=[C:16]([CH3:18])[CH:17]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 13066113Cyclopentyl methanesulfonateHCID 57414918(S)-methyl 2-(6-((4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 73388924(S)-methyl 2-(6-((4'-(cyclopentyloxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetateYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Cyclopentyl methanesulfonate 10c (50 mg, 0.28 mmol), (S)-methyl 2-(6-((4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3 h (60 mg, 0.14 mmol), and cesium carbonate (100 mg, 0.30 mmol) were dissolved in 10 mL of N,N-dimethylformamide. The reaction mixture was heated to 80° C. and stirred for 12 hours. The resulting mixture was mixed with 10 mL of water and extracted with ethyl acetate (20 mL×2). The organic phase was washed with water (20 mL×2) and saturated sodium chloride solution (20 mL) successively, dried with anhydrous sodium sulfate, and filtered. The filtrate was concentrated under the reduced pressure and the residue was purified by elution system B to obtain the title compound (S)-methyl 2-(6-((4′-(cyclopentyloxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 10d (40 mg, yield 30.0%) as a colorless slime.

Workup

  1. extractionextracted with ethyl acetate (20 mL×2)
  2. washThe organic phase was washed with water (20 mL×2) and saturated sodium chloride solution (20 mL) successively
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under the reduced pressure
  6. customthe residue was purified by elution system B

Sources & evidence

ORD record
ord-689dee51956d4620b4e5fea72547cfd4
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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