Water → HCID 71087288, compound

HRID 242376Notes

Reaction equation

HRID 242376 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([CH2:9][OH:10])[N:6]=[CH:5]1)([CH3:3])[CH3:2].[CH3:11][C:12]([Si:15](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:14])[CH3:13].O>ClC(Cl)C.CN(C1C=CN=CC=1)C>[Si:15]([O:10][CH2:9][C:7]1[N:6]=[CH:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH:8]=1)([C:12]([CH3:14])([CH3:13])[CH3:11])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 23343272HCID 23343272, compound

Product 1

HCID 71087288HCID 71087288, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

This (1-isopropyl-1H-imidazol-4-yl)methanol was dissolved in dichloroethane (200 mL), and at room temperature TEA (10.9 mL), TBDPSCl (10.2 mL) and DMAP (0.320 g) were added, followed by stirring for 17 hours. The reaction solution was poured into water, and extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=20%→100%) using silica gel column (product name: Hi-Flash Column 3 L, manufactured by Yamazen Corporation) to afford the title compound (9.11 g).

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationsubsequently the solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=20%→100%)

Sources & evidence

ORD record
ord-dc5de84cc126417d8483a2d42a7dbf49
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Reaction notes

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