Pinacolone → HCID 57890134, compound

HRID 1819961Notes

Reaction equation

HRID 1819961 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](=[O:5])[CH3:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Br-].[CH2:19]([C:21]([C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[C:32]([CH3:37])[CH:31]=1)([C:24]1[S:25][CH:26]=[C:27]([CH3:29])[CH:28]=1)[CH2:22][CH3:23])[CH3:20].C1COCC1>C1COCC1.CCOC(C)=O>[CH2:19]([C:21]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:4][C:3](=[O:5])[C:2]([CH3:7])([CH3:6])[CH3:1])=[C:32]([CH3:37])[CH:31]=1)([C:24]1[S:25][CH:26]=[C:27]([CH3:29])[CH:28]=1)[CH2:22][CH3:23])[CH3:20]

Participants

6

Reactant 3

HCID 6416PinacoloneHCID 2733832Lithium HexamethyldisilazideHCID 131727660HCID 131727660, compound

Product 1

HCID 57890134HCID 57890134, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of {4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenyl}-methanol (6 g,) in THF (50 ml) is treated with PBr3 (2.2 ml, 23.3 mmol) and warmed to RT. After stirring for 2 h, the mixture is partitioned between EtOAc and brine. The organic layer is MgSO4 dried, concentrated, and dissolved in anhydrous THF (30 ml) to give a solution of {4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenyl}-methane bromide. Separately, a solution of 3,3-dimethyl-butan-2-one (5.3 ml, 42.4 mmol) in THF (15 ml) is treated with LiHMDS (42.4 ml, 42.4 mmol, 1M in THF) at −70° C. for 1 h. This solution is transferred (via cannula) into a −70° C. solution of {4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenyl}-methanebromide/THF. The mixture is warmed to RT and stirred for 1 h. The reaction is diluted with EtOAc and washed with 0.2 N HCl until the aq layer is pH 2. The organic layer is concentrated to give the title compound (6.2 g, 79%).

Workup

  1. custominto a −70° C.
  2. washwashed with 0.2 N HCl until the aq layer
  3. concentrationThe organic layer is concentrated

Sources & evidence

ORD record
ord-7cf7fcc5af10402e8bd4c8795bf7ec09
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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