HCID 10873429, compound → HCID 89602475, compound

HRID 2201761Notes

Reaction equation

HRID 2201761 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[CH2:6]([O:13][C@H:14]([C@@H:17]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@@H:18]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:19]=[CH2:20])[CH:15]=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[CH2:6]([O:13][C@H:14]([C@@H:17]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C@@H:18]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:19]=[CH2:20])[CH:15]([OH:16])[CH2:3][CH:2]=[CH2:1])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 10873429HCID 10873429, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 89602475HCID 89602475, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Allyl magnesium bromide (1.0 M in Et2O, 1.44 mL, 1.44 mmol) was added dropwise over 5 min to a solution of aldehyde 47 (200 mg, 0.48 mmol) in THF (10 mL) at −78° C. The reaction mixture was left stirring at this temperature for 4 h before being quenched with NH4Cl solution (30 mL). The resulting layers were separated and the aqueous layer was extracted with EtOAc (3×25 mL). The combined organic layers were washed with H2O (20 mL) and brine (20 mL), dried over Na2SO4, filtered and the filtrate concentrated under reduced pressure. The crude product was purified by column chromatography (0-4% EtOAc in hexanes, gradient) to give product 53 as a mixture of two diasteroisomers.

Workup

  1. waitThe reaction mixture was left
  2. custombefore being quenched with NH4Cl solution (30 mL)
  3. customThe resulting layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×25 mL)
  5. washThe combined organic layers were washed with H2O (20 mL) and brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customThe crude product was purified by column chromatography (0-4% EtOAc in hexanes, gradient)

Sources & evidence

ORD record
ord-88e885630553498abbd8d9145b73b103
Source dataset
uspto-grants-2016_06
Patent number
US09365496B2

Reaction notes

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