1-Bromopropane → HCID 178450584, compound

HRID 2389199Notes

Reaction equation

HRID 2389199 reaction equation
Br[CH2:2][CH2:3]C.[CH2:5]([O:12][C@@H:13]1[CH2:18][CH2:17][C@H:16]([C:19](=[O:21])[CH3:20])[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1>[CH2:5]([O:12][C@@H:13]1[CH2:18][CH2:17][C@H:16]([C:19](=[O:21])[CH2:20][CH2:2][CH3:3])[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 78401-BromopropaneHCID 178468185HCID 178468185, compound

Product 1

HCID 178450584HCID 178450584, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of Mg (0.51 g, 21.6 mmol, 5.0 eq.) in dry THF (15 mL) under N2 was added 1-bromopropane (0.51 g, 2 mL, 5.0 eq.) dropwise and stirred at room temperature until Mg disappeared, then 1-(cis-4-(benzyloxy)cyclohexyl)ethanone (1.2 g, 4.3 mmol, 1.0 eq.) was added to the reaction mixture in an ice bath. The reaction mixture was warmed to r.t and stirred for 3 h., extracted (EtOAc), washed (brine), dried (Na2SO4), filtered and concentrated. The crude was then purified by silica gel chromatography eluting with EtOAc/Petroleum ether (10:1) to give the title compound (0.6 g, 50%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.34-7.24 (m, 5H), 4.49 (s, 2H), 3.62-3.60 (m, 1H), 2.44-2.40 (m, 2H), 2.34-2.33 (m, 1H), 1.98-1.80 (m, 4H), 1.64-1.46 (m, 6H), 0.89 (t, 3H).

Workup

  1. temperatureThe reaction mixture was warmed
  2. stirringstirred for 3 h.
  3. extractionextracted (EtOAc)
  4. washwashed (brine)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was then purified by silica gel chromatography
  9. washeluting with EtOAc/Petroleum ether (10:1)

Sources & evidence

ORD record
ord-688b8482c7c84299852cd4d5d81195e6
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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