tert-Butyldimethylsilyl chloride → HCID 19385582, compound

HRID 2399396Notes

Reaction equation

HRID 2399396 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.[CH:11](N(C(C)C)CC)(C)C.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[Br:1][CH:2]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])=[CH:5][CH:4]=1)[CH3:11]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 103304344-(Bromomethyl)benzyl alcohol

Product 1

HCID 19385582HCID 19385582, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Stir 1-bromomethyl-4-hydroxymethyl benzene (20.75 g)in CH2Cl2 (300 ml) with diisopropylethylamine (14.01 g) at 18° C., and add a solution of t-butyl dimethylsilyl chloride (16.34 g) in CH2Cl2 (100 ml). Stir for one half hour at room temperature, then reflux for 19 hours under a N2 atmosphere. Monitor reaction progress by TLC.

Workup

  1. temperaturereflux for 19 hours under a N2 atmosphere
  2. customMonitor reaction progress by TLC

Sources & evidence

ORD record
ord-80fd7e1d9c234de582f8d773c271cb27
Source dataset
uspto-grants-1995_09
Patent number
US05449680

Reaction notes

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