Potassium Carbonate → HCID 68525779, compound

HRID 2221306Notes

Reaction equation

HRID 2221306 reaction equation
CC1(C)O[C@@H](COS([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=O)=O)CO1.[C:20]1([S:26]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([Br:36])[CH:30]=2)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-:38].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[C:20]1([S:26]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:13][C@@H:12]3[CH2:17][CH2:16][C:15]([CH3:18])([CH3:14])[O:38]3)=[C:31]([Br:36])[CH:30]=2)(=[O:27])=[O:28])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6993835(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-ToluenesulfonateHCID 597108924-Benzenesulfonyl-2-bromo-phenol

Product 1

HCID 68525779HCID 68525779, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Toluene-4-(R)-sulfonic acid 2,2-dimethyl-[1,3]dioxolan-4-yl-methyl ester (0.99 g; 0.003 mol) was added to a suspension of 4-benzenesulfonyl-2-bromo-phenol (0.91 g; 0.003 mol, prepared by the procedure of Sung-Eun et al. as described in Example 1) and potassium carbonate (0.88 g; 0.0006 mol) in acetonitrile (4 mL). The mixture was heated under reflux for 72 hours. After cooling to ambient temperature the mixture was diluted with ethyl acetate, filtered, washed with water and saturated sodium bicarbonate, dried (Na2SO4) and concentrated in vacuo. The crude material was purified by crystallization from diethyl ether-hexane to give 4-(S)-(4-benzenesulfonyl-2-bromo-phenoxymethyl)-2,2-dimethy-[3,3]dioxolan as a white crystalline (1.41 g; 84%). Mp. 115.8-118.5° C., [α]=+20.2° (methanol; c=1).

Workup

  1. custom0.003 mol, prepared by the procedure of Sung-Eun et al.
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 72 hours
  4. filtrationfiltered
  5. washwashed with water and saturated sodium bicarbonate
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by crystallization from diethyl ether-hexane

Sources & evidence

ORD record
ord-5fafdc668f344fffa57050e304a6c781
Source dataset
uspto-grants-2008_05
Patent number
US07368567B2

Reaction notes

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