Dimethylformamide → HCID 11163965, compound

HRID 1017722Notes

Reaction equation

HRID 1017722 reaction equation
C([Li])(C)(C)C.CCCCC.[Si:11]([O:18][C:19]1[CH:20]=[C:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:22]=[CH:23][CH:24]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].CN(C)[CH:35]=[O:36]>C(OCC)C>[Si:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH:35]=[O:36])=[C:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8003PentaneHCID 17947803HCID 17947803, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 11163965HCID 11163965, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of tert-butyllithium in pentane (1.7 M, 21.8 mL, 37.1 mmol, 2.40 equiv) was added to a solution of tert-butyl 3-{[tert-butyl(dimethyl)silyl]oxy}phenyl carbamate (12-3, 5.00 g, 15.5 mmol, 1 equiv) in ethyl ether (150 mL) at −40° C., and the resulting mixture was stirred at −40° C. for 2 h. N,N-Dimethylformamide (9.57 mL, 124 mmol, 8.00 equiv) was added, and the mixture was then warmed to 0° C. The reaction mixture was partitioned between water (500 mL) and ethyl ether (500 mL). The organic layer was dried over sodium sulfate and concentrated, and the residue was purified by flash column chromatography (hexane, initially, grading to 20% hexane in EtOAc) to give tert-butyl 5-{[tert-butyl(dimethyl)silyl]oxy}-2-formylphenylcarbamate (12-4) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 10.34 (s, 1H), 9.54 (s, 1H), 7.76 (d, 1H, J=1.8 Hz), 7.26 (d, 1H, J=7.8 Hz), 6.35 (dd, 1H, J=7.8, 1.9 Hz), 1.37 (s, 9H), 0.78 (s, 9H), −0.02 (s, 6H).

Workup

  1. temperaturethe mixture was then warmed to 0° C
  2. customThe reaction mixture was partitioned between water (500 mL) and ethyl ether (500 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified by flash column chromatography (hexane

Sources & evidence

ORD record
ord-c7a94d5c2c2c4351bbe1bf9718d31385
Source dataset
uspto-grants-2002_11
Patent number
US06479512B1

Reaction notes

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