Isopropanol → 4-Oxetan-3-yl-3-(2-m-tolyl-ethoxy)-benzoic Acid Isopropyl Ester

HRID 1475743Notes

Reaction equation

HRID 1475743 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[C:6]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[CH:5]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl.N[C@@H]1CCCC[C@H]1O.I[CH:44]1[CH2:47][O:46][CH2:45]1.[CH3:48][CH:49]([OH:51])[CH3:50]>[Ni](I)I.CC(=O)OCC>[CH:49]([O:51][C:3](=[O:2])[C:4]1[CH:9]=[CH:8][C:7]([CH:44]2[CH2:47][O:46][CH2:45]2)=[C:6]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[CH:5]=1)([CH3:50])[CH3:48]

Participants

8

Reactant 5

HCID 3776Isopropanol2×HCID 2724254Sodium bis(trimethylsilyl)amideHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-HCID 133566863-IodooxetaneHCID 671695624-Borono-3-(2-m-tolyl-ethoxy)-benzoic Acid Methyl Ester

Product 1

HCID 671701384-Oxetan-3-yl-3-(2-m-tolyl-ethoxy)-benzoic Acid Isopropyl Ester

Reagents, catalysts & solvents 2

HCID 26038Nickel(II) iodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.0 g of 4-borono-3-(2-m-tolyl-ethoxy)-benzoic acid methyl ester, 51 mg of nickel iodide, 2.0 g of sodium bis(trimethylsilyl)amide and 25 mg of trans-2-aminocyclohexanol hydrochloride were placed into a microwave vial and 10 ml of anhydrous 2-propanol added. The mixture was stirred for 10 min. Then a solution of 1.0 g of 3-iodo-oxetane in 3 ml of anhydrous 2-propanol was added and the mixture reacted for 40 min at 80° C. under microwave irradiation. The mixture was then poured into 150 ml of EA and washed three times with 30 ml each of a saturated aqueous sodium hydrogensulfate solution and three times with 30 ml each of a saturated aqueous sodium carbonate solution. The organic layer was dried with magnesium sulfate and evaporated. Silica gel chromatography (EA/HEP 1:5) of the residue yielded 120 mg of the title compound.

Workup

  1. additionadded
  2. customthe mixture reacted for 40 min at 80° C. under microwave irradiation
  3. washwashed three times with 30 ml each of a saturated aqueous sodium hydrogensulfate solution and three times with 30 ml each of a saturated aqueous sodium carbonate solution
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-f6b392ab431747619532f46e7df4c1a6
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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