Hexane → HCID 19363547, compound

HRID 850324Notes

Reaction equation

HRID 850324 reaction equation
[CH3:1]CCCCC.C([Li])CCC.[CH3:12][O:13][C:14]1[CH:34]=[CH:33][C:17]([CH2:18][O:19][CH2:20][CH2:21][C:22](=O)[CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[CH:16][CH:15]=1.C(OCC)(=O)C.CCCCCC>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:12][O:13][C:14]1[CH:34]=[CH:33][C:17]([CH2:18][O:19][CH2:20][CH2:21][C:22]([CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[CH2:1])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 19363557HCID 19363557, compoundHCID 21226206Ethyl acetate hexaneHCID 178418339Butyllithium

Product 1

HCID 19363547HCID 19363547, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Combine methlytriphenylphosphonium bromide (3.08 g, 8.61 mmol) with THF (50 mL) and add a hexane solution of n-butyllithium (3.8 mL, 2.5 M, 9.47 mmol). After the addition is complete stir at ambient temperature for 0.5 hour. Add 4-(p-methoxybenzyloxy)-1-(t-butyldimethylsilyloxy)butan-2-one (2.65 g, 7.82 mmol) in THF (10 mL) and stir for 0.5 hours. Quench the reaction with saturated ammonium chloride solution and partition it between diethyl ether and water, wash the organic layer with water and then with saturated sodium chloride solution. Dry over MgSO4 and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/19 ethyl acetate/hexane to give the title compound as an oil. Rf =0.25; silica gel, 1/9 ethyl acetate/hexane. 1H NMR (CDCl3, 300 MHz) δ0.05 (s, 6H), 0.91 (s, 9H) 2.33 (t, J=6.98 Hz, 2H), 3.56 (t, J=6.98 Hz, 2H), 3.81 (s, 3H), 4.08 (s, 2H), 4.45 (s, 2H), 4.87 (s, 1H), 5.09 (d, J=1.65 Hz, 2H), 6.88 (d, J=8.73 Hz, 2H), 7.25 (d, J=8.73 Hz, 2H).

Workup

  1. additionAfter the addition
  2. customQuench
  3. customthe reaction with saturated ammonium chloride solution
  4. custompartition it between diethyl ether and water
  5. washwash the organic layer with water
  6. dry with materialDry over MgSO4
  7. concentrationconcentrate in vacuo
  8. customto give a residue

Sources & evidence

ORD record
ord-2ca55ccf65ec4819ac1aec6643b9c7d9
Source dataset
uspto-grants-2000_01
Patent number
US06017923

Reaction notes

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