tert-Butyldimethylsilyl chloride → HCID 19814454, compound

HRID 466823Notes

Reaction equation

HRID 466823 reaction equation
[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:13])[CH:11]=2)[N:6]=[C:5]([CH2:14][CH2:15][CH3:16])[C:4]=1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].CCOC(C)=O.C(Cl)Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:25]([O:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:13])[CH:11]=2)[N:6]=[C:5]([CH2:14][CH2:15][CH3:16])[C:4]=1[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([Br:24])=[CH:22][CH:23]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 19814443HCID 19814443, compoundHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 19814454HCID 19814454, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 50 mg (0.13 mmole) of 54 in 0.5 mL of CH2Cl2 containing 25 λ Et3N (17.5 mg; 0.17 mmole) and 10 mg DMAP (0.08 mmole) was added dropwise with stirring under a nitrogen atmosphere while cooling to 0° C., 25 mg (0.17 mmole) of t-butyldimethylsilyl chloride in 0.5 mL of CH2Cl2. After stirring overnight, the reaction mixture was washed with water, dried (MgSO4) and the product isolated by preparative tlc on silica gel GF using 5% EtOAc/CH2Cl2, giving clean 55.

Workup

  1. stirringAfter stirring overnight
  2. washthe reaction mixture was washed with water
  3. dry with materialdried (MgSO4)
  4. customthe product isolated by preparative tlc on silica gel
  5. customgiving clean 55

Sources & evidence

ORD record
ord-49cdd43dbec348a5905b754bc3b5f4de
Source dataset
uspto-grants-1992_10
Patent number
US05157040

Reaction notes

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