Water → HCID 18680340, compound

HRID 2417287Notes

Reaction equation

HRID 2417287 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C-:6]1[CH2:10][CH:9]=[CH:8][S:7]1.O.[CH2:12]([O:14][P:15]([O:19]CC)[O:16][CH2:17][CH3:18])[CH3:13]>>[CH2:12]([O:14][P:15]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)(=[O:19])[O:16][CH2:17][CH3:18])[CH3:13]

Participants

4

Reactant 3

HCID 962WaterHCID 31215Triethyl phosphiteHCID 86585305HCID 86585305, compound

Product 1

HCID 18680340HCID 18680340, compoundYield 82%

Procedure

A solution of 1d (4.58 g, 0.02 mol) in 20 mL of triethylphosphite was heated at 160° C. for 20 hours, with nitrogen bubbling directly into the solution. The solution was cooled to room temperature and 50 mL of water was added; the resulting mixture was stirred for 4 hours. The product was extracted with methylene chloride, the organic layer was separated and washed with brine, then dried over anhydrous magnesium sulfate. Evaporation of the solvent yielded an oily residue, which was distilled under vacuum (0.12 mm Hg, 135° C.) to give 1e as a colorless oil (6.0 g, 82%). 1H NMR (250 MHz, 25° C., CDCl3): δ 7.06 (m, 1H, Ar—H), 6.85 (m, 1H, Ar—H), 6.72 (m, 1H, Ar—H), 4.03 (m, 4H, POCH2CH3), 2.79 (t, 2H, Ar—CH2), 1.72 (m, 6H, CH2CH2CH2P), 1.26 (t, 6H, POCH2CH3).

Workup

  1. extractionThe product was extracted with methylene chloride
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent
  6. customyielded an oily residue, which
  7. distillationwas distilled under vacuum (0.12 mm Hg, 135° C.)

Sources & evidence

ORD record
ord-2c4e791b13df42348044b0633b6d2f58
Source dataset
uspto-grants-2004_11
Patent number
US06825358B2

Reaction notes

Loading…