Tempo → 4-Prop-2-ynylcyclohexanecarboxylic acid
Reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].C(OC1C(OC(=O)C)=C(I)C=CC=1)(=[O:14])C.CC1(C)N([O])C(C)(C)CCC1>C(#N)C.O>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:14])=[O:11])[CH2:6][CH2:5]1)[C:2]#[CH:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of Compound 9 (2.45 g, 16 mmol) in 50% acetonitrile/water (35 mL) cooled to 0° C. was added bis-acetoxy-iodobenzene (BAIB) (11.4 g, 35 mmol) and TEMPO (502 mg, 3.2 mmol). The reaction mixture was stirred at 0° C. for 1 hour, then for 90 minutes at room temperature. The solvents were evaporated, and the residue dissolved in 1/1 CH3CN/H2O (100 mL). Once again the solvents were evaporated, and this procedure repeated to remove iodobenzene as its azeotrope. The resulting Compound 11 (2.53 g, 95%) was obtained as a brown sticky solid that was not further purified but carried forward into the next step. 1H-NMR (600 MHz, CD3OD): 1.13 (dq, 2H), 1.45 (dq, 2H), 1.48 (m, 1H), 1.93 (dd, 2H), 2.03 (dd, 2H), 2.12 (dd, 2H), 2.2-2.3 (m, 2H).
Workup
- waitfor 90 minutes at room temperature
- customThe solvents were evaporated
- dissolutionthe residue dissolved in 1/1 CH3CN/H2O (100 mL)
- customOnce again the solvents were evaporated
- customto remove iodobenzene as its azeotrope
Sources & evidence
- ORD record
- ord-dee9fc0933ca4480ad8f475029cd4479
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07671191B2
Reaction notes
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