Sodium Acetate → (1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl acetate

HRID 1855035Notes

Reaction equation

HRID 1855035 reaction equation
CC1C=CC(S([O:11][CH2:12][C:13]23[CH2:20][CH2:19][C:16]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH:22]=4)([CH2:17][CH2:18]2)[O:15][CH2:14]3)(=O)=O)=CC=1.[C:34]([O-])(=[O:36])[CH3:35].[Na+]>CS(C)=O.CCOC(C)=O>[C:34]([O:11][CH2:12][C:13]12[CH2:18][CH2:17][C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:22]=3)([CH2:19][CH2:20]1)[O:15][CH2:14]2)(=[O:36])[CH3:35]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 90408232(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 90408674(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl acetate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate (0.1 g, 0.215 mmol) and sodium acetate (0.212 g, 2.58 mmol) in DMSO (5 mL) was stirred at 70° C. in a seal tube for 3 days. The reaction was diluted with EtOAc (5 mL) and washed with water (3×5 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give (1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl acetate. The mixture of the above acetate (0.076 g, 0.216 mmol) and 1 M NaOH (0.65 mL, 0.647 mmol) in THF/MeOH (1:1 of a 2 mL solution) was stirred at rt for 18 h. The reaction was diluted with EtOAc (5 mL) and washed with water (3×5 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude oil was purified by flash chromatography on SiO2 (0 to 50% EtOAc:hexanes) to afford the title compound (0.05 g, 75% yield) as a clear oil. 1H NMR (500 MHz, CDCl3) δ 7.39-7.26 (m, 3H), 7.21-7.14 (m, 2H), 7.14-7.08 (m, 1H), 7.05-7.00 (m, 2H), 6.88 (ddd, J=8.1, 2.5, 1.0 Hz, 1H), 3.99-3.89 (m, 2H), 3.38 (s, 2H), 2.16-2.00 (m, 4H), 1.84-1.71 (m, 3H), 1.71-1.57 (m, 2H).

Workup

  1. washwashed with water (3×5 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e655b5005a094f0da1c80e876d746f8d
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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