Triethylamine → HCID 13071254, compound

HRID 435409Notes

Reaction equation

HRID 435409 reaction equation
Cl[O:2][N:3]=[CH:4][C:5]1[C:6]([CH3:11])=[CH:7][CH:8]=[CH:9][CH:10]=1.[CH2:12]=[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:15](=[O:16])[O:14]1.C(N(CC)CC)C>CCOCC>[CH3:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]1[CH2:12][C:13]2([C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15](=[O:16])[O:14]2)[O:2][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 100576273-Methyleneisobenzofuran-1(3H)-oneHCID 53983756HCID 53983756, compound

Product 1

HCID 13071254HCID 13071254, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of o-tolualdehyde chlorooxime (26.8 g, 0.158 mole), 3-methylenephthalide (14.6 g, 0.1 mole) and ether (400 ml.) was added dropwise a solution of triethylamine (16 g, 0.158 mole) in 30 ml. of ether at 5°-10° C. in 45 minutes. The mixture was stirred at room temperature for 40 hours and filtered. The solid material collected was dissolved in 1 liter of chloroform and 200 ml. of water. The chloroform solution was then washed two times with water, dried over CaSO4 and concentrated under vacuum to give 16.4 g of white solid, m.p. 146°-149° C. The original ether solution was washed two times with water, dried over CaSO4 and concentrated to 100 ml. Another 1.64 g of the spiro compound precipitated out. The ether solution was then further concentrated to 10.8 g of yellow-brown oil which did not contain a significant amount of the desired product. Recrystallization of 12 g of the crude spiro compound from tetrahydrofuran-ether gave 9.87 g of a pure white solid, m.p. 159°-164° C. with decomposition.

Workup

  1. filtrationfiltered
  2. customThe solid material collected
  3. dissolutionwas dissolved in 1 liter of chloroform
  4. washThe chloroform solution was then washed two times with water
  5. dry with materialdried over CaSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f75323e008914209a6f0a0c51d21d7dc
Source dataset
uspto-grants-1983_08
Patent number
US04401457

Reaction notes

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