Imidazole → HCID 86693776, compound

HRID 245064Notes

Reaction equation

HRID 245064 reaction equation
[CH3:1][C:2]1[CH:3]([OH:7])[CH2:4][CH2:5][CH:6]=1.N1C=CN=C1.[C:13]([Si:17](Cl)([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)([CH3:16])([CH3:15])[CH3:14].O>CN(C)C1C=CN=CC=1.ClCCl>[C:13]([Si:17]([O:7][CH:3]1[CH2:4][CH2:5][CH:6]=[C:2]1[CH3:1])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 124809492-Methylcyclopent-2-en-1-ol

Product 1

HCID 86693776HCID 86693776, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methylcyclopent-2-en-1-ol (23.06 g, 235.0 mmol), 1H-imidazole (32.0 g, 470 mmol) and N,N-dimethyl-4-pyridinamine (5.74 g, 47.0 mmol) in dichloromethane (470 mL) at room temperature is added tert-butylchlorodiphenylsilane (90.41 g, 328.94 mmol) over 15 min. After stirring the reaction mixture at room temperature for 16 h, water (300 mL) is added and the layers are separated. The aqueous layer is extracted with dichloromethane (2×200 mL). The combined organic portions are dried over sodium sulfate, filtered, and concentrated to give the crude product (108 g) as a colorless oil. The crude product is purified in 20 g batches on 330 g silica gel using 0-20% dichloromethane/hexane (product observed on TLC using KMnO4 staining) to give the title compound as a colorless oil (25.3 g, 32%). 1H-NMR (400 MHz, CDCl3) δ 7.72-7.69 (m, 4H), 7.44-7.41 (m, 6H), 5.44-5.41 (m, 1H), 4.72-4.70 (m, 1H), 2.33-2.29 (m, 1H), 2.06-2.01 (m, 2H), 1.74-1.69 (m, 1H), 1.66-1.65 (m, 3H), 1.09 (s, 9H).

Workup

  1. customthe layers are separated
  2. extractionThe aqueous layer is extracted with dichloromethane (2×200 mL)
  3. dry with materialThe combined organic portions are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product (108 g) as a colorless oil
  7. customThe crude product is purified in 20 g batches on 330 g silica gel using 0-20% dichloromethane/hexane (product observed on TLC using KMnO4 staining)

Sources & evidence

ORD record
ord-a4257bc7c3494d29bfb58483eb796155
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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