Pyrrolidine → Methyl 3-(cyclopentenylmethylene)-4-oxochroman-7-carboxylate

HRID 505713ノート

反応式

HRID 505713 の反応式
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[C:16]1([CH:21]=O)[CH2:20][CH2:19][CH2:18][CH:17]=1.N1CCCC1>CO>[C:16]1([CH:21]=[C:3]2[C:2](=[O:1])[C:11]3[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=3)[O:5][CH2:4]2)[CH2:20][CH2:19][CH2:18][CH:17]=1

参加物

5

反応物 3

HCID 31268PyrrolidineHCID 1386721-Cyclopentene-1-carboxaldehydeHCID 11769654Methyl 4-oxochroman-7-carboxylate

生成物 1

HCID 66722625Methyl 3-(cyclopentenylmethylene)-4-oxochroman-7-carboxylate収率 65.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl 4-oxochroman-7-carboxylate (500 mg, 2.4 mmol) in methanol (5 mL) was added cyclopent-1-enecarbaldehyde (465 mg, 4.8 mmol) and pyrrolidine (0.40 mL, 4.8 mmol). The solution was stirred for one hour at ambient temperature. The resulting brown precipitate was collected by vacuum filtration and dried to give methyl 3-(cyclopentenylmethylene)-4-oxochroman-7-carboxylate (444 mg, 64% yield). LC/MS on 4.6×50 mm C-18 column, tR=6.49 minutes (10 to 90% acetonitrile/water over 8 minutes at 2 mL/minute with detection 254 nm, at 50° C.); ES-MS m/z 285 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.88-1.99 (m, 2H), 2.43 (d, J=13.16 Hz, 2H), 2.63 (t, J=6.98 Hz, 2H), 3.85 (s, 3H), 5.36 (s, 2H), 6.45 (br. s., 1H), 7.37 (s, 1H), 7.49 (d, J=1.34 Hz, 1H), 7.60 (dd, J=8.06, 1.61 Hz, 1H), 7.93 (d, J=8.32 Hz, 1H).

後処理

  1. filtrationThe resulting brown precipitate was collected by vacuum filtration
  2. customdried

出典と根拠

ORDレコード
ord-036226c09b8541a8b50685566c90c54e
出典データセット
uspto-grants-2010_08
特許番号
US07781428B2

反応ノート

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