Dimethylformamide → HCID 18404088, compound

HRID 1017717Notes

Reaction equation

HRID 1017717 reaction equation
C([Li])(C)(C)C.CCCCC.[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].CN(C)[CH:26]=[O:27]>C1COCC1>[CH:26]([C:13]1[CH:14]=[CH:15][S:11][C:12]=1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8003PentaneHCID 319413tert-Butyl thiophen-2-ylcarbamateHCID 178418306HCID 178418306, compound

Product 1

HCID 18404088HCID 18404088, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of tert-butyllithium in pentane (1.7 M, 35.4 mL, 60.2 mmol, 2.40 equiv) was added to a solution of tert-butyl 2-thienylcarbamate (10-2, 5.00 g, 25.1 mmol, 1 equiv) in THF (75 mL) at −78° C., and the resulting mixture was stirred at −78° C. for 1.5 h. N,N-Dimethylformamide (5.83 mL, 75.3 mmol, 3.00 equiv) was added, and the mixture was then warmed to 0° C. The reaction mixture was partitioned between water (300 mL) and EtOAc (2×200 mL). The combined organic layers were then dried over sodium sulfate and concentrated, and the residue was purified by flash column chromatography (hexane, initially, grading to 30% hexane in EtOAc) to give tert-butyl 3-formyl-2-thienylcarbamate (10-3) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 10.51 (s, 1H), 9.80 (s, 1H), 7.11 (d, 1H, J=5.7 Hz), 6.68 (d, 1H, J=5.9 Hz), 1.55 (s, 9H).

Workup

  1. temperaturethe mixture was then warmed to 0° C
  2. customThe reaction mixture was partitioned between water (300 mL) and EtOAc (2×200 mL)
  3. dry with materialThe combined organic layers were then dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified by flash column chromatography (hexane

Sources & evidence

ORD record
ord-05f93067334745ba8d01bd486694bfdb
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Reaction notes

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