HCID 59132627, compound → HCID 59132656, compound

HRID 1160303Notes

Reaction equation

HRID 1160303 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][Mg]Br.[CH3:7][O:8][C:9](=[O:32])[C:10](=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)=[CH:18][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12]>C1COCC1>[CH3:14][O:13][C:11](=[O:12])[CH:10]([CH:15]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)=[CH:18][CH:17]=1)[CH:1]=[C:2]([CH3:6])[CH3:3])[C:9]([O:8][CH3:7])=[O:32]

Participants

4

Reactant 2

HCID 59132627HCID 59132627, compoundHCID 178448304HCID 178448304, compound

Product 1

HCID 59132656HCID 59132656, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-methyl-1-propenylmagnesium bromide (3 mL, 0.5 M in THF) was added dropwise to a solution of compound 33.1 (1.0 mmol) in THF. The reaction mixture was stirred at room temperature for 1 hr and then quenched with saturated NH4Cl(aq) and the aqueous layer extracted with ethyl acetate twice. The combined organic layers were washed with water and saturated brine, dried over Na2SO4, and concentrated in vacuo. The resulting residue was purified using silica gel column chromatography (hexane/ethyl acetate=2/1) to give compound 33.2 as a white solid (0.93 mmol).

Workup

  1. customquenched with saturated NH4Cl(aq)
  2. extractionthe aqueous layer extracted with ethyl acetate twice
  3. washThe combined organic layers were washed with water and saturated brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-e1d8451e9d514dbebe3ab625c807a1fb
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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