Imidazole → HCID 14988196, compound

HRID 1708076Notes

Reaction equation

HRID 1708076 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.N1C=CN=C1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19].O>CN(C=O)C>[CH:18]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1)([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 108558177-hydroxy-2,3-dihydro-4H-chromen-4-one

Product 1

HCID 14988196HCID 14988196, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

7-Hydroxy-4-chromanone (1.2 g, 7.3 mmol; Dann et al., Ann. 587, 16, 1954) and imidazole (1.0 g, 14.7 mmol) were dissolved in DMF (10 ml). Triisopropylsilyl chloride (1.8 ml, 8.2 mmol) in DMF (2 ml) was added dropwise at ambient temperature over 10 minutes. After stirring for 3 hours, the mixture was poured onto 100 ml ice and water, and extracted with ether (2×100 ml). The combined ether extracts were washed with 1M LiCl and then brine, dried over CaSO4, and concentrated to a brown oil which was purified by Kugelrohr distillation (0.5 torr, 70°-90° C.). This removed a colorless, viscous oil impurity and left the brown oil product in the distillation pot (2.0 g, 85%). IR (KBr) 2945, 2867, 1685, 1605, 1268, 1163. HRMS Calcd. for MH+, 320.1807; observed, 320.1842.

Workup

  1. extractionextracted with ether (2×100 ml)
  2. washThe combined ether extracts were washed with 1M LiCl
  3. dry with materialbrine, dried over CaSO4
  4. concentrationconcentrated to a brown oil which
  5. distillationwas purified by Kugelrohr distillation (0.5 torr, 70°-90° C.)
  6. customThis removed a colorless, viscous oil impurity
  7. waitleft the brown oil product in the distillation pot (2.0 g, 85%)

Sources & evidence

ORD record
ord-35722fc9b46f40b386338c359c49f5f9
Source dataset
uspto-grants-1994_10
Patent number
US05356905

Reaction notes

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