Ammonium Chloride → HCID 19745859, compound

HRID 2253758Notes

Reaction equation

HRID 2253758 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)=[CH:15][CH:14]=2)=[O:12])=[CH:4][CH:3]=1.[CH2:31]([Mg]Br)[CH:32]=[CH2:33].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)=[CH:15][CH:14]=2)([OH:12])[CH2:33][CH:32]=[CH2:31])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 19745887HCID 19745887, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 19745859HCID 19745859, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ketone from Example 25, Step 1 (1.5 g, 3.61 mmol) in dry THF (15 mL) at 0° C. was added a 1M solution of allyl magnesium bromide (4.3 mL, 4.3 mmol). The reaction mixture was stirred for 45 minutes at 0° C., at which point saturated NH4Cl solution (15 mL) was added, and the product was extracted with EtOAc. The organic layer was washed with water and brine, and was then evaporated to dryness. Purification by flash chromatography (gradient of 1:20, 1:10, 1:5 EtOAc/hexane) gave a pale yellow syrup which was triturated with 1:4 ether/hexane to give the title compound as a white solid, m.p.=87°-88° C.

Workup

  1. additionwas added
  2. extractionthe product was extracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. customwas then evaporated to dryness
  5. customPurification by flash chromatography (gradient of 1:20, 1:10, 1:5 EtOAc/hexane)
  6. customgave a pale yellow syrup which
  7. customwas triturated with 1:4 ether/hexane

Sources & evidence

ORD record
ord-2baa3f3d6e8d4f338155bda2e3aa7445
Source dataset
uspto-grants-1993_08
Patent number
US05232916

Reaction notes

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