Tributylphosphine → 4-(benzyloxy)-8-methoxy-3-methyl-2-{[3-(tetrahydro-2H-pyran-4-ylmethoxy)phenoxy]methyl}quinoline

HRID 384474ノート

反応式

HRID 384474 の反応式
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[C:14]([O:19][CH3:20])[CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:21][OH:22])[C:10]=1[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:24]1[CH2:29][CH2:28][CH:27]([CH2:30][O:31][C:32]2[CH:33]=[C:34](O)[CH:35]=[CH:36][CH:37]=2)[CH2:26][CH2:25]1.C1CCN(C(/N=N/C(N2CCCCC2)=O)=O)CC1.C(P(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[C:14]([O:19][CH3:20])[CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:21][O:22][C:36]2[CH:35]=[CH:34][CH:33]=[C:32]([O:31][CH2:30][CH:27]3[CH2:26][CH2:25][O:24][CH2:29][CH2:28]3)[CH:37]=2)[C:10]=1[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 13831Tributylphosphine2 回HCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)HCID 59526840[4-(Benzyloxy)-8-methoxy-3-methylquinolin-2-yl]methanolHCID 595270023-[(Oxan-4-yl)methoxy]phenol

生成物 1

HCID 595271314-(benzyloxy)-8-methoxy-3-methyl-2-{[3-(tetrahydro-2H-pyran-4-ylmethoxy)phenoxy]methyl}quinoline収率 84.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of [4-(benzyloxy)-8-methoxy-3-methylquinolin-2-yl]methanol (250 mg) in THF (10 mL) were added 3-(tetrahydro-2H-pyran-4-ylmethoxy)phenol (185 mg) and 1,1-(azodicarbonyl)dipiperidine (245 mg), followed by dropwise addition of tributylphosphine (0.24 mL) at room temperature and stirring. After 1 hour, tributyl phosphine (0.24 mL) was added thereto, followed by stirring for 12 hours. Ethyl acetate was added to the reaction mixture, and then insolubles were removed by filtration. The filtrate was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography twice (eluent for the first round: hexane/ethyl acetate=80/20˜67/33˜60/40, eluent for the second round: chloroform˜chloroform/methanol=95/5), and also by thin layer silica gel chromatography (developer: chloroform/methanol=95/5) to obtain 4-(benzyloxy)-8-methoxy-3-methyl-2-{[3-(tetrahydro-2H-pyran-4-ylmethoxy)phenoxy]methyl}quinoline (340 mg).

後処理

  1. stirringby stirring for 12 hours
  2. custominsolubles were removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography twice (eluent for the first round: hexane/ethyl acetate=80/20˜67/33˜60/40, eluent for the second round: chloroform˜chloroform/methanol=95/5), and also by thin layer silica gel chromatography (developer: chloroform/methanol=95/5)

出典と根拠

ORDレコード
ord-9c11ebaf09d14182b9d690e72ce12321
出典データセット
uspto-grants-2013_02
特許番号
US08367702B2

反応ノート

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