Imidazole → HCID 68650408, compound

HRID 646729Notes

Reaction equation

HRID 646729 reaction equation
[OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH2:9][CH2:8]2.Cl[Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CN=C1>CN(C=O)C>[CH3:20][C:19]([Si:16]([CH3:18])([CH3:17])[O:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH2:9][CH2:8]2)([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68650633HCID 68650633, compound

Product 1

HCID 68650408HCID 68650408, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(Hydroxyprop-1-yn-1-yl)-2,3-dihydro-1H-indene-1-one (1.03 g, 5.42 mmol) was dissolved in DMF and treated with chloro-tert-butyldimethylsilane (981 mg, 6.51 mmol), imidazole (443 mg, 6.51 mmol) at 0° C. The reaction mixture was allowed to reach ambient temperature. After 10 h, the reaction mixture was extracted with ethyl acetate (100 mL×3), washed with water, brine and dried over MgSO4. The organic layer was concentrated under vacuum and purified by flash column chromatography to yield the 5-(3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}propyl)-2,3-dihydro-1H-inden-1-one (1.54 g, 94% yield): 1H NMR (400 MHz, CDCl3): δ 7.63 (d, 1H), 7.59 (s, 1H), 7.42 (d, 1H), 4.45 (t, 2H), 3.10 (m, 2H), 2.78 (m, 2H), 2.64 (m, 2H), 1.82 (m, 2H), 0.95 (s, 9H), 0.06 (s, 6H).

Workup

  1. customto reach ambient temperature
  2. extractionthe reaction mixture was extracted with ethyl acetate (100 mL×3)
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationThe organic layer was concentrated under vacuum
  6. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-dae13840d60d4eeabc2d5acefbe95619
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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