Dimethyl Sulfoxide → Ethyl 5-(1-acetyl-1H-indol-3-yl)pent-2-enoate

HRID 1198488ノート

反応式

HRID 1198488 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][CH2:24][CH2:25]O)=[CH:15]1)(=[O:13])[CH3:12].CCN(CC)CC.[C:34]([CH:39]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:36][CH2:37][CH3:38])=[O:35]>C(Cl)Cl.CCOCC>[CH2:37]([O:36][C:34](=[O:35])[CH:39]=[CH:25][CH2:24][CH2:23][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]([C:11](=[O:13])[CH3:12])[CH:15]=1)[CH3:38]

参加物

8

反応物 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 19380935HCID 19380935、化合物

生成物 1

HCID 53953280Ethyl 5-(1-acetyl-1H-indol-3-yl)pent-2-enoate収率 56.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirring solution of oxalyl chloride (11.4 mL, 0.13 mol) in CH2Cl2 (440 mL) at -78° C. was added dry DMSO (12.4 mL, 0.17 mol) dropwise. After 5 minutes, gas evolution ceased and the alcohol 4 (19 g, 87 mmol) in CH2Cl2 (40 mL) was added. After 30 minutes, NEt3 (73 mL, 0.52 mol) was added to effect a thick slurry. The cooling bath was removed and the reaction stirred for an additional 15 minutes before adding (carbethoxymethylene)triphenyl phosphorane (33.5 g, 96 mmol). After 2.0 hours, the reaction mixture was diluted with ether and then washed with H2O (2 times), 5% KHSO4 and brine, dried (MgSO4), and concentrated. Flash chromatography (20% ethyl acetate/hexanes) gave the olefin 5 (14 g) as a white solid. TLC Rf=0.54 (60% ethyl acetate/hexanes); 1H NMR (CDCl3) 8.42 (bd, 1H), 7.50 (d, J=7 Hz, 1H), 7.34 (t, J=7 Hz, 1H), 7.28 (t, J=7 Hz, 1H), 7.19 (bs, 1H), 7.03 (dt, J=18 and 7 Hz, 1H), 5.88 (d, J=18 Hz, 1H), 4.19 (q, J=7 Hz, 2H), 2.87 (t, J=7 HZ, 2H), 2.63 (m, 2H), 2.61 (s, 3H), 1.28 (t, J=7 Hz, 3H).

後処理

  1. waitAfter 30 minutes
  2. customThe cooling bath was removed
  3. waitAfter 2.0 hours
  4. washwashed with H2O (2 times), 5% KHSO4 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-7dbc55202df240a6b0437842c3c5a858
出典データセット
uspto-grants-1994_01
特許番号
US05281585

反応ノート

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