Diisopropylethylamine → Silane, [(3-bromo-3-butenyl)oxy](1,1-dimethylethyl)dimethyl-

HRID 1907402Notes

Reaction equation

HRID 1907402 reaction equation
[Br:1][C:2](=[CH2:6])[CH2:3][CH2:4][OH:5].FC(F)(F)S(O[Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])(=O)=O.CCN(C(C)C)C(C)C>ClCCl>[Br:1][C:2](=[CH2:6])[CH2:3][CH2:4][O:5][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 5339753-Bromo-3-buten-1-ol

Product 1

HCID 11129203Silane, [(3-bromo-3-butenyl)oxy](1,1-dimethylethyl)dimethyl-Yield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromobut-3-en-1-ol (5.2 g, 34.4 mmol) in dichloromethane (69 mL) at rt was added tert-Butyldimethylsilyl trifluoromethanesulfonate (10 g. 37.9 mmol) and DIEA (7.22 mL, 41.3 mmol) and the mixture was stirred at rt for 30 min. The reaction mixture was partitioned between dichloromethane and water, and the crude product obtained from the dichloromethane layer was purified by chromatography eluting with 5-30% EtOAc/Hexanes to give the title compound as a colorless liquid (8.72 g, 95%). 1H NMR (400 MHz, CDCl3) δ 5.66 (1H, s), 5.48 (1H, s), 3.81 (2H, t, J=6.0 Hz), 2.64 (2H, t, J=6.0 Hz), 0.91 (9H, s), and 0.09 (6H, s).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and water
  2. customthe crude product obtained from the dichloromethane layer
  3. customwas purified by chromatography
  4. washeluting with 5-30% EtOAc/Hexanes

Sources & evidence

ORD record
ord-2570e0c80b684c11bc558cb7f4362a7d
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

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