Propargyl alcohol → HCID 59372952、化合物

HRID 1471337ノート

反応式

HRID 1471337 の反応式
[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

参加物

4

反応物 2

HCID 7859Propargyl alcoholHCID 59373107HCID 59373107、化合物

生成物 1

HCID 59372952HCID 59372952、化合物収率 23.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-711ce33cfd7a494f9544d25ee5bcfc2b
出典データセット
uspto-grants-2015_04
特許番号
US09012217B2

反応ノート

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