Triethylamine → 61081-81-0

HRID 1643422Notes

Reaction equation

HRID 1643422 reaction equation
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.CCN(CC)CC.[N+:14]([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)([O-:16])=[O:15]>C(Cl)Cl>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([O:6][CH:1]2[CH2:5][CH:4]=[CH:3][CH2:2]2)=[O:22])=[CH:24][CH:25]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 2814783-Cyclopenten-1-ol

Product 1

HCID 6675178961081-81-0Yield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyclopentene-1-ol (7.0 g, 83.0 mmol) and Et3N (14.5 g, 143.0 mmol) in CH2Cl2 (200 mL) was added 4-nitrobenzoyl chloride (18.5 g, 100.0 mmol) as solid in several portions over a period of 30 min. The resulting suspension was stirred at room temperature over night. The precipitate was filtered off and the filtrate was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage SP1; column 40M; TLC method: n-hexane/ethyl acetate 9/1; Rf=0.50), affording the title product (15.6 g, yield 81%): 1H NMR (500 MHz, CDCl3) δ 8.28 (d, J=8.9 Hz, 2H), 8.20 (d, J=8.9 Hz, 2H), 5.81 (m, 2H), 5.69 (m, 1H), 2.95 (m, 2H), 2.61 (m, 2H).

Workup

  1. filtrationThe precipitate was filtered off
  2. washthe filtrate was washed with water and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (Biotage SP1; column 40M; TLC method: n-hexane/ethyl acetate 9/1; Rf=0.50)

Sources & evidence

ORD record
ord-e1a27d88cccd44feb777028b2c0d3e87
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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