Hydrochloric Acid → HCID 70022690, compound

HRID 989615Notes

Reaction equation

HRID 989615 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH2:18][CH2:17][CH:16]([OH:23])[CH2:15][C:14]=1[CH2:13][CH:12]=3)(=[O:3])[CH3:2].N1C=CN=C1.[Si:29](Cl)([C:42]([CH3:45])([CH3:44])[CH3:43])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl>ClCCl>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH2:18][CH2:17][CH:16]([O:23][Si:29]([C:42]([CH3:45])([CH3:44])[CH3:43])([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:15][C:14]=1[CH2:13][CH:12]=3)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 59913818HCID 59913818, compound

Product 1

HCID 70022690HCID 70022690, compoundYield 115.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the alcohols 10 (1.08 g, 3.42 mmol) in dichloromethane (20 mL) was added imidazole (1.6 eq, 0.37 g, 5.43 mmol) followed by tert-butyldiphenylsilylchloride (1.6 eq, 1.42 mL, 3.64 mmol). The mixture was stirred 16 h at room temperature under nitrogen then poured into 1N HCl (100 mL). The layers were separated and the aqueous layer was extracted with ether (3×50 mL). The organic layers were combined, washed with saturated aqueous NaCl solution (50 mL), dried over magnesium sulfate and concentrated under reduced pressure to give an oil (2.2 g), Rf 0.55 (10% EtOAc/hexane), which was used without further purification.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ether (3×50 mL)
  3. washwashed with saturated aqueous NaCl solution (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91a0e61d3a6342289beaa4cd7982dea0
Source dataset
uspto-grants-2002_10
Patent number
US06458778B1

Reaction notes

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