4-Iodo-1-tritylimidazole → (2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol

HRID 1174672Notes

Reaction equation

HRID 1174672 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C([Mg]Br)C.[O:30]1[C:35]2[CH:36]=[CH:37][CH:38]=[C:39]([CH:40]=[O:41])[C:34]=2[O:33][CH2:32][CH2:31]1>ClCCl>[O:30]1[C:35]2[CH:36]=[CH:37][CH:38]=[C:39]([CH:40]([C:2]3[N:3]=[CH:4][N:5]([C:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:6]=3)[OH:41])[C:34]=2[O:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 27950332,3-Dihydro-1,4-benzodioxine-5-carbaldehyde2×HCID 178418443HCID 178418443, compound

Product 1

HCID 59749547(2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-iodo-1-tritylimidazole (commercially available) (8.64 g, 19.8 mmol) in dichloromethane (100 mL) at −10° C. was treated with ethyl magnesium bromide (6.3 mL, 19 mmol, 3M in THF) and allowed to react for 45 m. A solution of 2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde (Intermediate A2) (2.6 g, 15.9 mmol) in dichloromethane was added via syringe at −10° C. and stirred for 45 m. The mixture was quenched with water (50 mL) and a sat. solution of ammonium chloride (50 mL). The residue was isolated in a typical aqueous workup and purified by chromatography on silica gel with 3 to 5% NH3-MeOH:CH2Cl2 to give (2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol (Intermediate A3) as a solid, 2.9 g (40%).

Workup

  1. customto react for 45 m
  2. customThe mixture was quenched with water (50 mL)
  3. customThe residue was isolated in a typical aqueous workup
  4. custompurified by chromatography on silica gel with 3 to 5% NH3-MeOH

Sources & evidence

ORD record
ord-e5d5df73fcf941c496cb9ce2cb5cec02
Source dataset
uspto-grants-2010_11
Patent number
US07838545B2

Reaction notes

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