Imidazole → HCID 11047330, compound

HRID 404309Notes

Reaction equation

HRID 404309 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[C:12]([Si:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)Cl)([CH3:15])([CH3:14])[CH3:13].N1C=CN=C1>CN(C=O)C>[Si:16]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 70206596-Hydroxy-1-indanone

Product 1

HCID 11047330HCID 11047330, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-hydroxy-1-indanone (250 g, 1687 mmol) (634549, commercially available from Sigma-Aldrich, St. Louis, Mo., USA), t-butyldiphenylchlorosilane (487 g, 1772 mmol) and imidazole (138 g, 2025 mmol) in degassed DMF (900 mL) was heated at 60° C. for 16 hours. The mixture was then concentrated to remove most of DMF, diluted with ether (3000 mL), filtered, and concentrated to give the initial product H1.1 (674 g, 100% yield) which was used in the next step reaction without further purification. MS ESI (pos.) M/E: 409 (M+Na).

Workup

  1. concentrationThe mixture was then concentrated
  2. customto remove most of DMF
  3. additiondiluted with ether (3000 mL)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-385235a86ec848c79c53b6aef75bd169
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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