Triethylamine → HCID 59557786, compound

HRID 425092Notes

Reaction equation

HRID 425092 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]([O:20][CH:21](OCC)[CH3:22])[CH3:19])=[CH:12][CH:11]=2)[CH:3]=1.C(N(CC)CC)C.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[OH-].[Na+]>ClCCl.C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]([O:20][CH:21]=[CH2:22])[CH3:19])=[CH:12][CH:11]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 65367Trimethylsilyl triflateHCID 59557744HCID 59557744, compound

Product 1

HCID 59557786HCID 59557786, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-1-chloro-2-(4-(2-(1-ethoxyethoxy)propoxy)benzyl)-benzene (550 mg, 1.3 mmol) in dichloromethane (10 mL) at 0° C. under argon was added triethylamine (0.2 mL, 2.2 mmol), followed by trimethylsilyltrifluoromethane sulfonate (240 mg, 2.2 mmol). After 1 h, 1.0 M sodium hydroxide (4 mL) was added, followed by diethyl ether (20 mL). The organic phase was separated, dried over sodium sulfate and concentrated to an oil, which was purified by column chromatography (PE/EA=10:1) to obtain intermediate DA (290 mg, yield 59%).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to an oil, which
  4. customwas purified by column chromatography (PE/EA=10:1)
  5. customto obtain intermediate DA (290 mg, yield 59%)

Sources & evidence

ORD record
ord-3a33484e52a843e792c8e00610498f41
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

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