Water → HCID 12660316, compound

HRID 554496Notes

Reaction equation

HRID 554496 reaction equation
CSC.C([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)C1C=CC=CC=1.O>C(Cl)Cl>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[OH:11])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1068Dimethyl SulfideHCID 674589421-Benzyloxy-2-(4-chlorobenzyl)benzene

Product 1

HCID 12660316HCID 12660316, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, dimethylsulfide (105.1 μL, 2.43 mmol) and a boron trifluoride-diethyl ether complex (51.3 μL, 0.4 mmol) were added to a solution of 1-benzyloxy-2-(4-chlorobenzyl)benzene (50.0 mg, 0.16 mmol) in methylene chloride (2.0 mL) under cooling with ice, and the reaction mixture was stirred for 19 hours while gradually raising its temperature to room temperature. Thereafter water was added thereto under cooling with ice and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:5)] to obtain the title compound (33.4 mg, 94%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. distillationthe solvent was distilled under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:5)]

Sources & evidence

ORD record
ord-d0545b48ce754072968dae9f87d96f01
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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