Imidazole → HCID 22951510, compound

HRID 275825Notes

Reaction equation

HRID 275825 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[O:5][CH2:6][C:7]1([O:23][CH2:22][CH2:21][O:20]1)[CH2:8][CH2:9][C@@H:10]1[C@@H:17]2[C@@H:13]([O:14][C:15](=[O:18])[CH2:16]2)[CH2:12][C@H:11]1[OH:19].N1C=CN=C1.[Si:32](Cl)([C:45]([CH3:48])([CH3:47])[CH3:46])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[Cl-].[NH4+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:19]([C@@H:11]1[CH2:12][C@@H:13]2[O:14][C:15](=[O:18])[CH2:16][C@@H:17]2[C@H:10]1[CH2:9][CH2:8][C:7]1([O:23][CH2:22][CH2:21][O:20]1)[CH2:6][O:5][C:4]1[CH:24]=[CH:25][CH:26]=[C:2]([Cl:1])[CH:3]=1)[Si:32]([C:45]([CH3:48])([CH3:47])[CH3:46])([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 59878880HCID 59878880, compound

Product 1

HCID 22951510HCID 22951510, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 10 (700 mg, 1.89 mmol), DMAP (58 mg, 0.48 mmol), and imidazole (192 mg, 2.82 mmol) in methylene chloride (11 mL) was added t-butyldiphenylsilyl chloride (670 mg, 2.45 mmol). After 4.5 h, saturated ammonium chloride (15 mL) was added, the phases were separated, the aqueous layer was extracted with methylene chloride (2×15 mL), the combined organic layers were dried (magnesium sulfate), filtered, concentrated, and chromatographed on a 22 cm tall×26 mm diameter silica gel column eluting with 40% ethyl acetate in hexane to afford 11 (951 mg, 83%).

Workup

  1. customthe phases were separated
  2. extractionthe aqueous layer was extracted with methylene chloride (2×15 mL)
  3. dry with materialthe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on a 22 cm tall×26 mm diameter silica gel column
  7. washeluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b0b5586dc9d0443f9a437d4d6f2bfd07
Source dataset
uspto-grants-2002_03
Patent number
US06353014B1

Reaction notes

Loading…