Hydrochloric Acid → HCID 131728087, compound

HRID 645457Notes

Reaction equation

HRID 645457 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]1[CH2:24][CH2:23][C@@:22]([C@@H:26]([CH3:34])[CH2:27][CH2:28][C@@H:29](O)[CH:30]([CH3:32])[CH3:31])([CH3:25])[C:21]1([CH3:36])[CH3:35])([C:14]([CH3:17])([CH3:16])[CH3:15])(C1C=CC=CC=1)C1C=CC=CC=1.N1[CH:41]=[CH:40]N=C1.[Si:42](Cl)([C:55]([CH3:58])([CH3:57])[CH3:56])([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.Cl>N1C=CC=CC=1.C(OCC)C.O>[C:14]([SiH2:1][O:18][C:19]([C:41]1[CH:40]=[CH:51][CH:50]=[CH:49][CH:54]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH:20]1[CH2:24][CH2:23][C:22]([CH:26]([CH3:34])[CH2:27][CH2:28][CH:29]([Si:42]([C:55]([CH3:56])([CH3:57])[CH3:58])([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:30]([CH3:32])[CH3:31])([CH3:25])[C:21]1([CH3:35])[CH3:36])([CH3:17])([CH3:15])[CH3:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 11613140HCID 11613140, compound

Product 1

HCID 131728087HCID 131728087, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of intermediate (16) (0.045 g, 0.088 mmol) and imidazole (0.0252 g, 0.366 mmol) in dry pyridine (1 mL) was added tert-butyl-diphenylsilyl chloride (97 μL, 0.366 mmol) at 20° C. and the reaction mixture was stirred for 48 hours. Water (30 mL) and diethyl ether (30 mL) were added and the mixture was neutralized to pH=6 using a 1 N hydrogen chloride solution. The aqueous layer was extracted with diethyl ether and the combined organic layers were dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the residue was purified over silica (isooctane/ethyl acetate, 98:2) and then used directly in the next step.

Workup

  1. extractionThe aqueous layer was extracted with diethyl ether
  2. dry with materialthe combined organic layers were dried over anhydrous MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified over silica (isooctane/ethyl acetate, 98:2)

Sources & evidence

ORD record
ord-0ec9cfad2f174117a5e06bc998b79960
Source dataset
uspto-grants-2010_04
Patent number
US07704986B2

Reaction notes

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