Propargyl alcohol → HCID 59372952, 화합물

HRID 1471337노트

반응식

HRID 1471337 반응식
[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

참가 물질

4

반응물 2

HCID 7859Propargyl alcoholHCID 59373107HCID 59373107, 화합물

생성물 1

HCID 59372952HCID 59372952, 화합물수율 23.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-711ce33cfd7a494f9544d25ee5bcfc2b
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012217B2

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