Imidazole → 2,5,7-Trimethyl-2-triethylsilanyloxymethyl-6-vinyl-indan-1-ol

HRID 473071Notes

Reaction equation

HRID 473071 reaction equation
[OH:1][CH2:2][C:3]1([CH3:17])[CH2:11][C:10]2[C:5](=[C:6]([CH3:15])[C:7]([CH:13]=[CH2:14])=[C:8]([CH3:12])[CH:9]=2)[CH:4]1[OH:16].N1C=CN=C1.[Si:23](Cl)([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25]>C(Cl)Cl.O>[CH3:17][C:3]1([CH2:2][O:1][Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:11][C:10]2[C:5](=[C:6]([CH3:15])[C:7]([CH:13]=[CH2:14])=[C:8]([CH3:12])[CH:9]=2)[CH:4]1[OH:16]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 59415730HCID 59415730, compound

Product 1

HCID 684751572,5,7-Trimethyl-2-triethylsilanyloxymethyl-6-vinyl-indan-1-olYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To the stirred solution of starting material 7 (0.85 g, 3.66 mmol) in dry CH2Cl2 added Imidazole (0.5 g, 7.32 mmol) and TESCl (0.6 mL, 3.66 mmol) sequentially at 0° C. under argon atmosphere and stirred the reaction mixture at same temperature for 6 h. Then reaction mixture was diluted with H2O (10 mL) followed by extraction with CH2Cl2 (50 mL), brine (25 mL), dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 5 to 10% EtOAc in petroleum ether eluant) gave pure compound 8 (0.85 g, 88%) as syrup.

Workup

  1. customThen reaction mixture
  2. extractionfollowed by extraction with CH2Cl2 (50 mL), brine (25 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (SiO2, 5 to 10% EtOAc in petroleum ether eluant)

Sources & evidence

ORD record
ord-16743c616dea49a9862844f9a4e5463c
Source dataset
uspto-grants-2014_01
Patent number
US08633252B2

Reaction notes

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