Imidazole → HCID 11044317, compound

HRID 2215831Notes

Reaction equation

HRID 2215831 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].N1C=CN=C1.C(Cl)Cl>CCCCCC>[C:15]([Si:12]([O:5][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:2][Cl:1])([CH3:14])[CH3:13])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 5720643-Chloro-1-phenylpropanol

Product 1

HCID 11044317HCID 11044317, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

3-Chloro-1-phenyl-propan-1-ol (3.87 g, 22.6 mmol), tert-butyldimethylsilyl chloride (3.75 g, 24.9 mmol), imidazole (2.00 g, 29.3 mmmol), and methylene chloride (50 mL) are combined and stirred for 1 hour. The mixture is quenched with saturated aqueous sodium bicarbonate and diluted with methylene chloride (100 mL). The mixture is washed with saturated aqueous ammonium chloride, water, and brine, then is dried over magnesium sulfate, filtered, and concentrated to a crude oil. Purification by flash chromatography, eluting with ethyl acetate:hexane gave 4.82 g (75% yield) of the title compound as a transparent oil. 1HNMR (DMSO-d6) 7.76–7.84 (m, 4H), 7.68–7.74 (m, 1H), 5.39 (dd, J=4, 4 Hz, 1H), 4.19–4.22 (m, 1H), 4.00–4.08(m, 1H), 2.55–2.65 (m, 1H), 2.38–2.48 (m, 1H), 1.34 (s, 9H), 0.53 (s, 3H), 0.28 (s, 3H).

Workup

  1. customThe mixture is quenched with saturated aqueous sodium bicarbonate
  2. additiondiluted with methylene chloride (100 mL)
  3. washThe mixture is washed with saturated aqueous ammonium chloride, water, and brine
  4. dry with materialis dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a crude oil
  7. customPurification by flash chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d2917f53f11f4b85a5f309ac871bc291
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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