Triethylamine → HCID 67127113, compound

HRID 514141Notes

Reaction equation

HRID 514141 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([CH:19]([OH:22])[CH:20]=[CH2:21])[C:3]=1[CH3:23].C(N(CC)CC)C.[Si:31](OS(C(F)(F)F)(=O)=O)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>C(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([CH:19]([O:22][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH:20]=[CH2:21])[C:3]=1[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonate2×HCID 67126210HCID 67126210, compound

Product 1

HCID 67127113HCID 67127113, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring 23° C. DCM solution (32 mL) of 1-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)prop-2-en-1-ol (1.47 g, 3.79 mmol) and triethylamine (2.3 mL, 16.5 mmol) was added TBDMS-OTf (2.0 mL, 11.65 mmol) and the reaction was stirred and monitored by TLC. After 45 minutes, an additional 2 mL of TBDMSOTf was added and the mixture allowed to stir overnight. The dark mixture was then quenched 10% NaHCO3 and the color dissipated. The mixture was washed with brine, dried with sodium sulfate and concentrated in vacuo. Column chromatography using silica gel with EtOAc in hexanes gave desired silylated product (1.60 g, 84% yield). 1H-NMR: (400 MHz, CDCl3): δ 8.39 (d, J=8.4 Hz, 1H); 7.55-745 (m, 3H); 7.34-7.30 m, 1H); 7.26-7.24 (m, 1H); 7.24-7.18 (d, J=8.0 Hz, 1H); 7.16-7.14 (m, 1H); 6.09-6.01 (m, 1H); 5.32-5.30 (m, 1H); 5.13-5.03 (m, 2H); 2.77 (s, 3H); 0.87 (s, 6H); 0.83 (s, 9H).

Workup

  1. customTo a stirring 23° C
  2. stirringto stir overnight
  3. customThe dark mixture was then quenched 10% NaHCO3
  4. washThe mixture was washed with brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8468cc532514bdab929b42ca0f3aa1f
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

Loading…