Pyrrole-2-carboxaldehyde → tert-Butyl 2-formyl-1H-pyrrole-1-carboxylate

HRID 865703노트

반응식

HRID 865703 반응식
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].[O:8](C(OC(C)(C)C)=O)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=O>CN(C1C=CN=CC=1)C.C1COCC1>[C:12]([O:11][C:9]([N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7])=[O:8])([CH3:15])([CH3:14])[CH3:13]

참가 물질

5

반응물 2

HCID 13854Pyrrole-2-carboxaldehydeHCID 90495Di-tert-butyl dicarbonate

생성물 1

HCID 5057005tert-Butyl 2-formyl-1H-pyrrole-1-carboxylate수율 107.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of pyrrole-2-carboxaldehyde (9.5 g, 0.1 mol), (BOC)2O (24.0 g, 0.11 mol) and DMAP (0.25 g) in THF (150 ml) was stirred at room temperature for 16 h. The solvent was removed under vacuum and the residue dissolved in CH2Cl2 (200 ml) and washed with 10% citric add, water and brine. The organic layer was dried (Na2SO4) and evaporated to give the desired product (20.9 g, 95%); δ (360 MHz, CDCl3) 1.65 (9H, s, 3 of CH3), 6.28-6.30 (1H, m, Ar--H), 7.18-7.19 (1H, m, Ar--H), 7.43-7.45 (1H, m, Ar--H). 2. trans-Methyl-2-N-tert-butyloxycarbonylpyrrol-2-yl)acrylate Prepared from the preceding aldehyde and methyl diethylphosphonoacetate as described for Intermediate 4 (step 3). The product (98%) was obtained as a pale yellow oil; δ (360 MHz, CDCl3) 1.63 (9H, s, 3 of CH3), 3.78 (3H, s, CH3), 6.21 (1H, d, J=16.0 Hz, vinyl CH), 6.21-6.22 (1H, m, Ar--H), 6.69-6.71 (1H, m, Ar--H), 7.38-7.39 (1H, m, Ar--H), 8.30 (1H, d, J=16.0 Hz, vinyl CH).

후처리

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue dissolved in CH2Cl2 (200 ml)
  3. washwashed with 10% citric add, water and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-2d5a7eb759684717901c09a36379c62e
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05567726

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