Water → HCID 86701857, compound

HRID 1844097Notes

Reaction equation

HRID 1844097 reaction equation
[O:1]=[C:2]1[N:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]2[C:12]3[C:17]([CH2:18][CH:4]2[CH2:3]1)=[CH:16][CH:15]=[CH:14][CH:13]=3.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:29](OCC)=[O:30].O>O1CCCC1>[OH:30]/[CH:29]=[C:3]1\[CH:4]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:5]2[N:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]\1=[O:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8025Ethyl formateHCID 2733832Lithium HexamethyldisilazideHCID 86701858HCID 86701858, compound

Product 1

HCID 86701857HCID 86701857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Ethyl 2-oxo-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrole-1-carboxylate (200 mg, 0.81 mmol) was dissolved in tetrahydrofuran (8 mL) was cooled to −78° C. Then, lithium bis(trimethylsilyl)amide (1 mol/L in THF, 1.22 mL, 1.22 mmol) was added. After 1 h at −78° C., ethyl formate (0.198 mL, 2.446 mmol) was added. The mixture was stirred for another 30 min and then allowed to warm to room temperature. After another 30 min, water was added. The mixture was extracted with diethylether, the pH of the aqueous layer was adjusted to 1 and the solution was extracted with EtOAc (2*20 mL), dried (Na2SO4) and concentrated to give a colourless oil ethyl (3E)-3-(hydroxymethylene)-2-oxo-4,8b-dihydro-3aH-indeno[1,2-b]pyrrole-1-carboxylate D12 (120 mg, 54%) which was used without further purification in the next step. LCMS (Method A): RT: 1.53 min; ES− 272 [M−H]

Workup

  1. temperatureto warm to room temperature
  2. waitAfter another 30 min
  3. extractionThe mixture was extracted with diethylether
  4. extractionthe solution was extracted with EtOAc (2*20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ca11ea1fe2d247cd82b561677895103d
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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