Propargyl alcohol → HCID 59372952, compound

HRID 1471337Notes

Reaction equation

HRID 1471337 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].Br[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([Cl:17])=[N:9][N:8]=1>O1CCCC1>[Cl:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([CH2:6][O:4][CH2:1][C:2]#[CH:3])=[N:8][N:9]=1

Participants

4

Reactant 2

HCID 7859Propargyl alcoholHCID 59373107HCID 59373107, compound

Product 1

HCID 59372952HCID 59372952, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of propargyl alcohol (46 mg, 0.81 mmol) and KN(TMS)2 (1.63 mL, 0.81 mmol) in tetrahydrofuran (1.5 mL) is stirred under argon for 30 min before 1-bromomethyl-4-chlorophthalazine (2) (140 mg, 0.54 mmol) is added. The mixture is stirred for 3 h, quenched with 2 N HCl (5 mL) and H2O (15 mL), and extracted with ethyl acetate (80 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (20% to 25% ethyl acetate/hexane) to give 29 mg (23%) of 3 as a colorless solid, mp 131-132° C. IR 3079, 1406, 1325 cm−1; 1H NMR (CDCl3) δ 2.60 (t, J=2.4 Hz, 1H, CH≡CCH2O), 5.17 (s, 2H, CH2), 5.36 (d, J=2.4 Hz, CH≡CCH2O), 7.90-8.02 (m, 2H, 6,7-PhthH), 8.21 (m, 1H, 5-PhthH), 8.36 ppm (m, 1H, 8-PhthH).

Workup

  1. additionis added
  2. customquenched with 2 N HCl (5 mL) and H2O (15 mL)
  3. extractionextracted with ethyl acetate (80 mL)
  4. washThe extract is washed (brine)
  5. customdried
  6. customAfter solvent removal at reduced pressure
  7. customthe residue is purified on silica gel (20% to 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-711ce33cfd7a494f9544d25ee5bcfc2b
Source dataset
uspto-grants-2015_04
Patent number
US09012217B2

Reaction notes

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