Diethyl Ether → HCID 59678602, compound

HRID 1751851Notes

Reaction equation

HRID 1751851 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)[C:2]#[C:3]C.C([Li])CCC.[CH3:21][O:22][C:23]1[C:32]([CH:33]=[O:34])=[C:31]([N+:35]([O-:37])=[O:36])[CH:30]=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27]([CH3:39])([CH3:38])[O:28]2.CCOCC>C1COCC1.O=[Mn]=O>[CH3:15][O:14][C:8]1[CH:7]=[C:6]([O:5][CH2:1][C:2]#[C:3][C:33]([C:32]2[C:23]([O:22][CH3:21])=[C:24]3[C:29](=[CH:30][C:31]=2[N+:35]([O-:37])=[O:36])[O:28][C:27]([CH3:39])([CH3:38])[CH:26]=[CH:25]3)=[O:34])[CH:11]=[CH:10][C:9]=1[O:12][CH3:13]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 59678695HCID 59678695, compoundHCID 59678709HCID 59678709, compoundHCID 178418339Butyllithium

Product 1

HCID 59678602HCID 59678602, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-but-2-ynyloxy-1,2-dimethoxy-benzene (1.66 g, 8.66 mmol) in THF (75 mL) is added n-butyl lithium (5.54 ml of 1.6 M solution in THF, 8.86 mmol) at −78° C. After 30 min., 5-methoxy-2,2-dimethyl-7-nitro-2H-chromene-6-carbaldehyde (2.17 g, 8.25 mmol) in THF (50 mL) is added. The reaction is stirred for 1 h and then quenched with sat. NH4Cl and extracted with ethyl acetate. The combined organic layers are washed with brine and dried over Na2SO4. The resulting crude material is dissolved in dichloromethane (20 mL) and MnO2 (5.3 g, 61 mmol) is added. After the reaction is stirred overnight at room temperature, ether is added and the suspension is filtered through a pad of celite and silica gel to afford 4-(3,4-dimethoxy-phenyoxy)-1-(5-methoxy-2,2-dimethyl-7-nitro-2H-chromen-6-yl)-but-2-yn-1-one.

Workup

  1. customquenched with sat. NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over Na2SO4
  5. dissolutionThe resulting crude material is dissolved in dichloromethane (20 mL)
  6. stirringAfter the reaction is stirred overnight at room temperature
  7. filtrationthe suspension is filtered through a pad of celite and silica gel

Sources & evidence

ORD record
ord-33850791fad748c78a41d928af7b3e12
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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