Potassium Carbonate → HCID 23655157, compound

HRID 2220588Notes

Reaction equation

HRID 2220588 reaction equation
[CH3:1]C(C)C(=O)C(P(=O)([O-])[O-])=[N+]=[N-].[CH:13]([CH2:15][CH2:16][C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][C:20]=2[CH:21]=1)=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH2:16]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][C:20]=2[CH:21]=1)[CH2:15][C:13]#[CH:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23657705HCID 23657705, compoundHCID 86586111Dimethyl-1-diazo-2-oxopropylphosphonate

Product 1

HCID 23655157HCID 23655157, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

See Callant, P. D. H. L.; Vandewalle, M. An efficient preparation and the intramoleucalur cyclopropanation of a-diazo-b-ketophosphonates and a-diazophoshonoacetates. Snyth. Commun. 1984, 14, 155-161. A solution of dimethyl-1-diazo-2-oxopropylphosphonate (8.9 g, 46.4 mmol) in dry methanol (50 mL) was added to a stirring mixture of 97 (8.5 g, 36.6 mmol) and K2CO3 (10.2 g, 74 mmol) in 500 mL of dry methanol. The mixture was stirred at room temperature until complete conversion was attained according to HPLC (2 hours) and concentrated. The residue was diluted with diethyl ether (500 mL), washed with water (2×100 mL) and dried over CaCl2. The solvent was removed following by recrystallization (EtOAc/hexanes, 9/1) to give white crystals (7.66 g, 92%): mp 57-58° C. 1H NMR (DMSO-d6) δ8.23 (d, J=1.6 Hz, 1H), 7.88 (dd, J=8.8, 1.6 Hz, 1H), 7.63 (d, J=8.8 Hz, 1H), 6.82 (s, 1H), 3.86 (s, 3H), 3.00 (t, J=7.1 Hz, 2H), 2.84 (t, J=2.8 Hz, 1H), 2.63 (td, J=7.1, 2.8 Hz, 2H). HPLC (method B) tR 6.73 min (100.00 area %). Anal. (C14H12O3.0.2H2O) C, H.

Workup

  1. customAn efficient preparation
  2. customwas attained according to HPLC (2 hours)
  3. concentrationconcentrated
  4. additionThe residue was diluted with diethyl ether (500 mL)
  5. washwashed with water (2×100 mL)
  6. dry with materialdried over CaCl2
  7. customThe solvent was removed
  8. customfollowing by recrystallization (EtOAc/hexanes, 9/1)

Sources & evidence

ORD record
ord-99255ae9b2aa465e807f7a62bcc873e4
Source dataset
uspto-grants-2008_08
Patent number
US07417158B2

Reaction notes

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