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Ammonium Chloride → HCID 71270118, compound

HRID 927110
Notes
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Reaction equation

HRID 927110 reaction equation
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([C:23]#[CH:24])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[O:30]1[CH2:35][CH2:34][C:33](=[O:36])[CH2:32][CH2:31]1.[Cl-].[NH4+]>O1CCCC1>[CH2:16]([O:15][C:14]1[CH:13]=[C:12]([C:23]#[C:24][C:33]2([OH:36])[CH2:34][CH2:35][O:30][CH2:31][CH2:32]2)[N:11]=[N:10][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 866770253,4-Bis(benzyloxy)-6-ethynylpyridazine2×HCID 178418339Butyllithium

Product 1

HCID 71270118HCID 71270118, compoundYield 501%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

3,4-bis(Benzyloxy)-6-ethynylpyridazine (Intermediate 5; 3.0 g, 9.49 mmol) was dissolved in tetrahydrofuran (24 ml) under nitrogen atmosphere and the resulting solution was cooled to −78° C. n-Butyl lithium (23% solution in hexane; 7.92 ml, 28.48 mmol, 3.0 eq) was added slowly at −78° C., and the resulting mixture was allowed to stir for 30 minutes. Dihydro-2H-pyran-4(3H)-one (1.0 g, 10.44 mmol, 1.1 equiv.) was added slowly to reaction mass and the whole was allowed to warm to room temperature. The crude mixture was then poured into a saturated solution of aqueous ammonium chloride (300 ml) and product was extracted into ethyl acetate (100 ml×2). The organic layer was separated, washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (eluting with 0-30% ethyl acetate in hexane) to yield the desired material (2.0 g, 501% yield).

Workup

  1. additionwas added slowly at −78° C.
  2. extractionwas extracted into ethyl acetate (100 ml×2)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel (eluting with 0-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bb9d9ca9d41a4df7836d51eb2c26467e
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290456B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes