tert-Butyl (triphenylphosphoranylidene) acetate → 4-(7-methyl-1H-indazol-5-yl)-but-2-enoic Acid Tert-Butyl Ester

HRID 2099736ノート

反応式

HRID 2099736 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][CH:12]=O)[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[C:14]([O:18][C:19]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>O1CCCC1>[C:14]([O:18][C:19](=[O:20])[CH:21]=[CH:12][CH2:11][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([CH3:1])[CH:3]=1)[NH:9][N:8]=[CH:7]2)([CH3:17])([CH3:16])[CH3:15]

参加物

4

反応物 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 57794606(7-methyl-1H-indazol-5-yl)-acetaldehyde

生成物 1

HCID 690719374-(7-methyl-1H-indazol-5-yl)-but-2-enoic Acid Tert-Butyl Ester収率 51.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Tetrahydrofuran (8 mL) was added to a flask containing (7-methyl-1H-indazol-5-yl)-acetaldehyde (1.94 mmol, 1.0 equiv) and (tert-butoxycarbonyl-methylene)triphenylphosphorane (1.46 g, 3.88 mmol, 2.0 equiv) at room temperature under nitrogen. The resulting yellow solution was stirred overnight (15 h). LCMS indicated completion. The mixture was partitioned between water and ethyl acetate. The organic layer was separated and washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography to afford the desired product as a yellow oil (272 mg, 51.5% for two steps). MS (ESI) [M+H]+=273; 1H NMR (400 MHz, CDCl3) δ 12.3 (br., 1H), 8.06 (s, 1H), 7.36 (s, 1H), 7.04 (m, 1H), 6.96 (s, 1H), 5.74 (dd, J=15.6 and 1.6 Hz, 1H), 3.54 (d, J=6.8 Hz; 2H), 2.57 (s, 3H), 1.47 (s, 9H).

後処理

  1. customThe mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-fb52fe7e55494e9d93e057ec2d088ad2
出典データセット
uspto-grants-2009_08
特許番号
US07569578B2

反応ノート

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