Ammonium Chloride → HCID 86731004, compound

HRID 1852423Notes

Reaction equation

HRID 1852423 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCC([O-])(C)C.[Na+].O=[C:32]1[CH2:35][CH:34]([C:36]([O:38][CH3:39])=[O:37])[CH2:33]1.[Cl-].[NH4+]>C1C=CC=CC=1>[CH3:2][O:3][CH:4]=[C:32]1[CH2:35][CH:34]([C:36]([O:38][CH3:39])=[O:37])[CH2:33]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2733478Sodium 2-methylbutan-2-olateHCID 13992367Methyl 3-oxocyclobutane-1-carboxylate

Product 1

HCID 86731004HCID 86731004, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

To a suspension of methoxymethyltriphenylphosphonium chloride (1350 g, 3.90 mol) in anhydrous benzene (12 L), a solution of sodium tert-pentoxide (435 g, 3.90 mol) in anhydrous benzene (4 L) was added slowly under nitrogen atmosphere. The resulting red solution was stirred for 15 minutes at ambient temperature. Then, a solution of methyl 3-oxocyclobutanecarboxylate (250 g, 1.95 mol) in anhydrous benzene (1 L) was added slowly and the reaction mixture was heated at 70° C. for 2 hours. Saturated aqueous ammonium chloride (˜4 L) was added to the reaction mixture and extracted with diethyl ether (5 L). The organic layer was washed with water (5 L×2), brine (5 L), dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography over silica gel (mesh 60-120; eluent: 10% diethyl ether in hexane) to afford the title compound as a pale yellow liquid. 1H NMR (300 MHz, CDCl3): δ 2.89-2.92 (m, 2H), 2.96-3.0 (m, 2H), 3.14-3.17 (m, 1H), 3.56 (s, 3H), 3.70 (s, 3H), 5.81-5.83 (m, 1H). GC-MS: [M]+ m/z=156.

Workup

  1. temperaturethe reaction mixture was heated at 70° C. for 2 hours
  2. extractionextracted with diethyl ether (5 L)
  3. washThe organic layer was washed with water (5 L×2), brine (5 L)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography over silica gel (mesh 60-120; eluent: 10% diethyl ether in hexane)

Sources & evidence

ORD record
ord-60f11a5293bb464e9315b68a81402cf4
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

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