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

HRID 2099736

반응식

HRID 2099736 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fb52fe7e55494e9d93e057ec2d088ad2
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569578B2

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