Adamantanone → HCID 66726898, compound

HRID 710354Notes

Reaction equation

HRID 710354 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)[CH2:2][C:3]#[CH:4].[CH:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[C:13]1=[O:22])[CH2:19]2>C1COCC1>[I:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][C:3]#[C:4][C:12]23[CH2:21][CH:16]4[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]4)[CH:13]2[OH:22])[CH2:19]3)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 64151AdamantanoneHCID 87126622HCID 87126622, compound

Product 1

HCID 66726898HCID 66726898, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-(but-3-ynyl)-4-iodobenzene (0.36 g, 1.48 mmol) in anhydrous THF (0.5 ml) 2.8 M MeMgBr in THF (0.6 ml) was added at 0° C. under N2. After stirring for 0.5 h, the solution of 2-admantanone (0.24 g, 1.6 mmol) was added drop wise. This was stirred for 2 h at room temperature, than quenched with the solution of NH4Cl. The mixture was extracted with Et2O. The organic layer was dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2) to give the title product (0.34 g; 56%), as the creamy paste. 1H-NMR (CDCl3) 2.14-2.23 (m, 16H); 4.69 (s, 2H); 6.74 (d, 2H, J=6.87 Hz); 7.54 (d, 2H, J=6.81 Hz).

Workup

  1. stirringThis was stirred for 2 h at room temperature
  2. customthan quenched with the solution of NH4Cl
  3. extractionThe mixture was extracted with Et2O
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by FCC (SiO2)

Sources & evidence

ORD record
ord-68535c29ee4c4688948d6e3ccf114cda
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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