HCID 59749551, compound → HCID 68773320, compound

HRID 1174674Notes

Reaction equation

HRID 1174674 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([C:13]3[N:14]=[CH:15][N:16]([C:18]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:17]=3)=[O:12])[C:5]=2[O:4][CH2:3][CH2:2]1.[CH3:37][Mg+].[Br-]>C1COCC1.CCOCC>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([C:13]3[N:14]=[CH:15][N:16]([C:18]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:17]=3)([OH:12])[CH3:37])[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 59749551HCID 59749551, compound2×HCID 178418689HCID 178418689, compound

Product 1

HCID 68773320HCID 68773320, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanone (Intermediate B1) (0.91 g, 1.93 mmol) in THF (80 mL) at −10° C. was treated with MeMgBr (2.6 mL, 7.68 mmol of a 3M solution in Et2O) for 45 m. The mixture was quenched with a sat. solution of NH4Cl and water. The layers were separated and the organic layer dried over MgSO4. The suspension was filtered and evaporated to dryness. The material was purified by chromatography on SiO2 with 50% EtOAc in CHCl3 to give 1-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-1-(1-trityl-1H-imidazol-4-yl)-ethanol as a foam 0.95 g (98%).

Workup

  1. customThe mixture was quenched with a sat. solution of NH4Cl and water
  2. customThe layers were separated
  3. dry with materialthe organic layer dried over MgSO4
  4. filtrationThe suspension was filtered
  5. customevaporated to dryness
  6. customThe material was purified by chromatography on SiO2 with 50% EtOAc in CHCl3

Sources & evidence

ORD record
ord-fa75a00225af4a0a8b993f4db9e334c2
Source dataset
uspto-grants-2010_11
Patent number
US07838545B2

Reaction notes

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