tert-Butyldiphenylchlorosilane → HCID 68313753, compound

HRID 1527136Notes

Reaction equation

HRID 1527136 reaction equation
[C@@H:1]1([N:9]2[C:13]3=[N:14][CH:15]=[N:16][C:17]([O:18][CH3:19])=[C:12]3[C:11]([I:20])=[N:10]2)[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.[C:21]([Si:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)Cl)([CH3:24])([CH3:23])[CH3:22]>N1C=CC=CC=1>[Si:25]([CH:7]([OH:8])[C@H:5]1[O:6][C@@H:1]([N:9]2[C:13]3=[N:14][CH:15]=[N:16][C:17]([O:18][CH3:19])=[C:12]3[C:11]([I:20])=[N:10]2)[CH2:2][C@@H:3]1[OH:4])([C:21]([CH3:24])([CH3:23])[CH3:22])([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 94078tert-ButyldiphenylchlorosilaneHCID 10644199HCID 10644199, compound

Product 1

HCID 68313753HCID 68313753, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 500 mL flask was suspended 2 (3.6 g, 9.2 mmol) in anhydrous pyridine (60 mL), then tert-butyldiphenylchlorosilane (2.78 g, 10 mmol) was added and the mixture stirred for 72 hours. The suspension was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with 10% citric acid, brine, dried over MgSO4, and concentrated to a white foam. The crude product was purified by flash chromatography with 25-33% ethyl acetate in hexanes to obtain 3 as a white foam (5.2 g, 90% yield).

Workup

  1. customIn a 500 mL flask was suspended
  2. concentrationThe suspension was concentrated
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with 10% citric acid, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a white foam
  7. customThe crude product was purified by flash chromatography with 25-33% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b52c14bb570548a2a9da6e4a60c4ad1f
Source dataset
uspto-grants-2015_07
Patent number
US09085800B2

Reaction notes

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