HCID 69706416, compound → HCID 86586629, compound

HRID 1359591Notes

Reaction equation

HRID 1359591 reaction equation
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([O:7][CH2:8][CH:9]=[CH:10][C:11]([O:13][CH3:14])=[O:12])=[C:5](I)[CH:4]=1)#[N:2]>C1COCC1.CCOCC>[C:1]([C:3]1[CH:16]=[CH:15][C:6]2[O:7][CH2:8][CH:9]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH:4]=1)#[N:2]

Participants

3

Reactant 1

HCID 69706416HCID 69706416, compound

Product 1

HCID 86586629HCID 86586629, compoundYield 137.4%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

To a cooled (−100° C.) solution of methyl 4-[4-cyano-2-iodo-phenoxy]-but-2-enoate (4.3 g, 12.5 mmol) (reference example 1 a) in THF: Et2O (4:1, 125 mL) was added dropwise n-buLi (5.5 mL, 2.5 M in hexanes). On complete addition, the reaction mixture was stirred for 15 min then quenched with 1 M aqueous HCl (20 mL). This mixture was diluted with ethyl acetate and washed, sequentially, with water and brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography (eluting with 25% ethyl acetate in hexanes) to give 3.73 g of the title compound. 1H NMR (CDCl3) d 2.63 (dd, 16, 8 Hz, 1H), 2.80 (dd, J=16, 5 Hz, 1H), 3.74 (s, 3H), 3.91 (m, 1H), 4.35 (dd, J=8, 6 Hz, 1H), 4.86 (t, J=8 Hz, 1H), 6.84 (d, J=8 Hz, 1H), 7.47 (m, 2H). MS (EI) m/z 203 (M)+. MS (EI) m/z 217 (M)+.

Workup

  1. additionOn complete addition
  2. customthen quenched with 1 M aqueous HCl (20 mL)
  3. additionThis mixture was diluted with ethyl acetate
  4. washwashed
  5. dry with materialsequentially, with water and brine, dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (eluting with 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f69ba945559f469c8203c21613a80aa6
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Reaction notes

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