Isopropanol → HCID 58611868, compound

HRID 2375228Notes

Reaction equation

HRID 2375228 reaction equation
[C:1]([O:5][C:6]([C:8]1([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH:34](O)([CH3:36])[CH3:35]>ClCCl.CN(C)C1C=CN=CC=1.C1C=CC=CC=1>[C:1]([O:5][C:6]([C:8]1([C:14]2[CH:15]=[CH:16][C:17]([C:18]([O:20][CH:34]([CH3:36])[CH3:35])=[O:19])=[CH:21][CH:22]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 58611848HCID 58611848, compound

Product 1

HCID 58611868HCID 58611868, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-[1-(tert-butoxycarbonyl)cyclohexyl]benzoic acid (12) (0.219 g, 0.72 mmol) in dichloromethane (5 ml) under argon atmosphere at ice bath temperature oxalyl chloride (0.3 ml, 3.44 mmol) and a drop of dimethylformamide were added. The reaction mixture was stirred at ambient temperature for 15 minutes and at 40° C. for 1 hour, then the volatiles were evaporated and the residue was dried in vacuo. The residue (0.247 g) was dissolved in tetrahydrofuran (4 ml) and 4-dimethylaminopyridine (0.176 g, 1.43 mmol) and isopropanol (0.35 ml, 4.57 mmol) were added to the resulting solution. The mixture was stirred overnight, supplemented with benzene (50 ml), successively washed with water (30 ml), brine (20 ml), and dried (Na2SO4). The solvents were evaporated and the residue was chromatographed on silica gel with toluene-ethyl acetate (97:3) as eluent to give the title compound (0.226 g, 91%) as an oil. 1H NMR (CDCl3, HMDSO) δ: 1.01-1.87 (8H, m); 1.34 (6H, d, J=6.5 Hz); 1.34 (9H, s); 2.17-2.61 (2H, m); 5.23 (1H, sept, J=6.5 Hz); 7.46 (2H, d, J=8.8 Hz); 7.98 (2H, d, J=8.8 Hz).

Workup

  1. customthe volatiles were evaporated
  2. customthe residue was dried in vacuo
  3. dissolutionThe residue (0.247 g) was dissolved in tetrahydrofuran (4 ml)
  4. stirringThe mixture was stirred overnight
  5. washsuccessively washed with water (30 ml), brine (20 ml)
  6. dry with materialdried (Na2SO4)
  7. customThe solvents were evaporated
  8. customthe residue was chromatographed on silica gel with toluene-ethyl acetate (97:3) as eluent

Sources & evidence

ORD record
ord-e61bc8f6064447939a75d0b52e57868a
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

Loading…