tert-Butyldimethylsilyl chloride → HCID 57706379, compound

HRID 1662411Notes

Reaction equation

HRID 1662411 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:28][C:27]([Si:24]([CH3:26])([CH3:25])[O:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])=[C:11]([C:18](=[O:23])[C:19]([CH3:20])([CH3:22])[CH3:21])[CH:12]=1)([CH3:30])[CH3:29]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 574675911-(2'-Fluoro-4-(hydroxymethyl)-5'-(methyloxy)-1,1'-biphenyl-2-yl)-2,2-dimethyl-1-propanone

Product 1

HCID 57706379HCID 57706379, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 66.13F (1.00 g, 3 mmol) in DCM (10.00 mL) at 23° C. was added tert-butyldimethylsilyl chloride (0.6 mL, 4 mmol), followed by TEA (0.5 mL, 4 mmol) and DMAP (0.04 g, 0.3 mmol). The reaction was stirred for 16 hours and then the reaction was concentrated in vacuo. The product was purified on silica gel (0-10% EtOAc in hexanes) to yield 66.30A as a colorless oil (1.30 g, 96% yield).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customThe product was purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-aec6498366d943c7b28f437b1ebf51b1
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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