Potassium Carbonate → HCID 178472523, compound

HRID 1969505Notes

Reaction equation

HRID 1969505 reaction equation
[OH:1][C@@H:2]1[CH2:5][C@H:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1>CN(C=O)C>[C:23]([C:22]1[CH:25]=[CH:26][C:19]([CH2:18][O:1][C@@H:2]2[CH2:5][C@H:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]2)=[CH:20][CH:21]=1)#[N:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 178472520HCID 178472520, compound

Product 1

HCID 178472523HCID 178472523, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of cis-ethyl 3-hydroxycyclobutanecarboxylate (0.17 g, 1.2 mmol) in DMF (4 mL) was added K2CO3 (0.24 g, 1.8 mmol) followed by 4-(bromomethyl)benzonitrile (0.28 g, 1.4 mmol). The reaction was stirred at about 25° C. for about 16 h. The reaction was partitioned between EtOAc (50 mL) and brine (50 mL). The layers were separated and the organic layer was washed with additional brine (50 mL). The organic layer was then dried over anhydrous Na2SO4, filtered, and concd in vacuo to give cis-ethyl 3-(4-cyanobenzyloxy)-cyclobutanecarboxylate (0.29 g, 95%) as an oil: 1H NMR (DMSO-d6) δ 7.82 (d, J=8.5 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 4.75 (s, 2H), 4.02 (q, J=7.1 Hz, 2H), 3.93 (m, 1H), 2.58-2.45 (m, 1H), 2.41-2.28 (m, 2H), 1.98-1.85 (m, 2H), 1.20-1.08 (t, J=7.1 Hz, 3H).

Workup

  1. customThe reaction was partitioned between EtOAc (50 mL) and brine (50 mL)
  2. customThe layers were separated
  3. washthe organic layer was washed with additional brine (50 mL)
  4. dry with materialThe organic layer was then dried over anhydrous Na2SO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4f1bc0a4f6384902bacf9e029540cdf0
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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