Triethylamine → HCID 90280212, compound

HRID 1506651Notes

Reaction equation

HRID 1506651 reaction equation
[OH:1][N:2]=[C:3](Cl)/[CH:4]=[CH:5]\[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[CH:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>C[C]1[C](C)[C](C)[C](C)[C]1C.C1CC=CCCC=C1.Cl[Ru]>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:3](/[CH:4]=[CH:5]/[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[N:2][O:1][CH:21]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70118Benzene, 1-chloro-4-ethynyl-HCID 90280186HCID 90280186, compound

Product 1

HCID 90280212HCID 90280212, compound

Reagents, catalysts & solvents 1

HCID 178420236HCID 178420236, compoundCatalyst

Procedure

A screw-top Schlenk flask (250 mL) purged with dry nitrogen was charged with compound 25B (7.31 g, 40 mmol) and 4-chlorophenylacetylene (5.0 g, 36.6 mmol). At room temperature, degassed 1,2-dichloroethane (100 mL) was added followed by [Cp*RuCl(cod)] (450 mg, 1.18 mmol) and triethylamine (6.38 mL, 45.8 mmol). The flask was purged with N2 and capped. After being stirred at room temperature for 7 h, the reaction mixture was passed through a plug of silica gel, and washed with DCM. The resulting solution was concentrated and the residue was purified by column chromatography on silica gel (pure hexanes to 10:1 hexanes/EtOAc) to provide the desired compound. MS (m/z) 282.0 [M+H]+.

Workup

  1. customA screw-top Schlenk flask (250 mL) purged with dry nitrogen
  2. customAt room temperature, degassed 1,2-dichloroethane (100 mL)
  3. additionwas added
  4. customThe flask was purged with N2
  5. customcapped
  6. washwashed with DCM
  7. concentrationThe resulting solution was concentrated
  8. customthe residue was purified by column chromatography on silica gel (pure hexanes to 10:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-ac0191918bcb4ae2a7dc8c00f62c67b0
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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