Hexane → HCID 22868719, compound

HRID 54157Notes

Reaction equation

HRID 54157 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].C([Cu])#N.[C:9]1([C:15]2[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:19]3[O:27][CH2:28][O:29][C:18]3=[CH:17][C:16]=2[CH2:30][C@@H:31]2[O:33][CH2:32]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCCCCC>CCCCC.C1COCC1>[CH3:2][C:1]([CH3:4])([CH3:3])[CH2:32][C@@H:31]([OH:33])[CH2:30][C:16]1[CH:17]=[C:18]2[O:29][CH2:28][O:27][C:19]2=[C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 22868720HCID 22868720, compoundHCID 178418306HCID 178418306, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 22868719HCID 22868719, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

t-Butyl lithium (21.4 mL of a 1.7M solution in pentane, 36.4 mmol) was added dropwise to a suspension of CuCN (1.63 g, 18.2 mmol) in 120 mL of THF at -78° C. The mixture was stirred for 30 min and allowed to warm to -10° C. A soultion of 8.01 g (2S)-3-(2,3-diphenylmethylenedioxyphenyl)-1,2-epoxypropane (24.2 mmol) of (from step 3 above) in 20 mL of THF was added dropwise. The reactions was stirred for 18 hr, then quenched by addition of 100 mL of 9:1 saturated NH4Cl: conc. NH4OH. The mixture was stirred vigorously for 30 min and partitioned between 50 mL of water and 150 mL of ether. The aqueous phase was extracted twice with 50 mL of ether, and the combined layers were washed with water and saturated NH4Cl and dried over MgSO4. The solvents were removed under vacuum to give an amber oil. The oil was purified by flash chromatography over silica gel, eluting with 20% ethyl acetate:hexane to afford 5.95 g (63% yield) of the title compound as a yellow oil. MS (DCI/NH3) M/Z: 389 (M+H)+, 406 (M+NH4)+. 1H NMR (CDCl3, 300 MHz) δ: 0.95 (s, 9H), 1.45 (m, 2H), 2.73 (dd, 1H), 2.85 (dd, 1H), 4.08 (m, 1H), 6.65-6.8 (m, 3H), 7.37 (m, 6H), 7.57 (m, 4H).

Workup

  1. stirringThe reactions was stirred for 18 hr
  2. customquenched by addition of 100 mL of 9:1 saturated NH4Cl
  3. stirringThe mixture was stirred vigorously for 30 min
  4. custompartitioned between 50 mL of water and 150 mL of ether
  5. extractionThe aqueous phase was extracted twice with 50 mL of ether
  6. washthe combined layers were washed with water and saturated NH4Cl
  7. dry with materialdried over MgSO4
  8. customThe solvents were removed under vacuum
  9. customto give an amber oil
  10. customThe oil was purified by flash chromatography over silica gel
  11. washeluting with 20% ethyl acetate

Sources & evidence

ORD record
ord-6f9c2ed1d98149a0a9e9264a4c9c28db
Source dataset
uspto-grants-1997_04
Patent number
US05621133

Reaction notes

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