Potassium Carbonate → HCID 57545169, compound

HRID 1661521Notes

Reaction equation

HRID 1661521 reaction equation
[I-].[I-].[Sm+2].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C@:11]2([C@H:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:28][CH:29]=[O:30])[C:15](=[O:16])[C:14]3[C:17]([O:24][CH2:25][CH3:26])=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[CH:20][C:13]=3[O:12]2)=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C@:11]23[C@H:27]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:28][C@H:29]([OH:30])[C@@:15]2([OH:16])[C:14]2[C:17]([O:24][CH2:25][CH3:26])=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[CH:20][C:13]=2[O:12]3)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57545213HCID 57545213, compoundHCID 178506586HCID 178506586, compound

Product 1

HCID 57545169HCID 57545169, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

178 ml (17.9 mmol) of a 0.1 M solution of samarium diiodide in THF is cooled to 0° C. under argon, and a solution of 2.60 g (5.10 mmol) of (S*,R*)-3-[2-(4-bromophenyl)-4,6-diethoxy-3-oxo-2,3-dihydrobenzofuran-2-yl]-3-phenylpropanal in 30 ml of degassed THF is added dropwise. The mixture is stirred at 0° C. for 1 h and at RT for 1 h. An ice-cold saturated sodium potassium tartrate solution with 10% potassium carbonate is added, the phases are separated, the aqueous phase is extracted three times with dichloromethane, and the combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Column chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate 95:5) results in 1.55 g (58% of theory) of the product as racemic mixture.

Workup

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted three times with dichloromethane
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customColumn chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate 95:5) results in 1.55 g (58% of theory) of the product as racemic mixture

Sources & evidence

ORD record
ord-a5358a944746455a863d7726f9042285
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

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