Thionyl Chloride → HCID 66777786, compound

HRID 2091407Notes

Reaction equation

HRID 2091407 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)O)=[C:14]([CH3:25])[C:13]=2[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:29])=O.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]([Cl:29])[CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:14]([CH3:25])[C:13]=2[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66777714HCID 66777714, compound

Product 1

HCID 66777786HCID 66777786, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [5-(benzyloxy)-3-methyl-1-benzofuran-2-yl](cyclohexyl)methanol (25.17 g) synthesized above in tetrahydrofuran (250 mL) was added thionyl chloride (9.44 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 hr. To the reaction mixture was added aqueous sodium hydrogen carbonate solution cooled to 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated to give the title compound (25.39 g, 96%) as a yellow solid.

Workup

  1. temperaturecooled to 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-008add1b90d3456392ee9f934058c0af
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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