Hydrochloric Acid → HCID 67324697, compound

HRID 1616909Notes

Reaction equation

HRID 1616909 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]#[N:13])(=O)OCC)C.[I:14][C:15]1[CH:24]=[CH:23][C:18]2C(=O)[CH2:20][O:21][C:17]=2[CH:16]=1.Cl>C1COCC1.O.CC(OC)(C)C>[I:14][C:15]1[CH:24]=[CH:23][C:18]2[C:11]([C:12]#[N:13])=[CH:20][O:21][C:17]=2[CH:16]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 75676Diethyl (cyanomethyl)phosphonateHCID 454897966-Iodo-1-benzofuran-3(2H)-one

Product 1

HCID 67324697HCID 67324697, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

Sodium hydride (37.3 g; 0.886 mol; 1.2 eq; 60 wt % dispersion in oil) was suspended in hexanes (120 mL) under N2. The sodium hydride was allowed to settle and the hexanes were syringed out of the flask and dry THF (100 mL) added. The NaH was washed again and the THF decanted. A fresh portion of dry THF (300 mL) was added and diethylcyanomethylphosphonate (0.886; 1.2 eq) was added drop wise over 35 min while keeping the temperature at 20-22° C. A solution of 6-iodo-1-benzofuran-3(2H)-one (192.0 g; 0.74 mol) in THF (1.75 L) then added over 35 min at 15-25° C. After 30 min stirring, 6N HCl (750 mL), MTBE (750 mL), and H2O (500 mL) were added. The layers were separated, sodium sulfate was added to the organic layer. The organics were filtered and concentrated. The resulting red solids were suspended in MTBE (500 mL), washed four times with 1N HCl (400 mL). The solvent was evaporated to afford 214 g of the title product. 1H-NMR (400 MHz, CDCl3): δ 3.75 (bs, 1H), 7.34 (d, 1H), 7.60 (s, 1H), 7.62 (dd, 1H), 7.91 (d, 1H).

Workup

  1. additionadded
  2. washThe NaH was washed again
  3. customthe THF decanted
  4. additionA fresh portion of dry THF (300 mL) was added
  5. customat 20-22° C
  6. customThe layers were separated
  7. additionsodium sulfate was added to the organic layer
  8. filtrationThe organics were filtered
  9. concentrationconcentrated
  10. washwashed four times with 1N HCl (400 mL)
  11. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0b2a603dd8ed4ceba29f50afe541da1e
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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