Dimethylformamide → HCID 90423560, compound

HRID 2272455Notes

Reaction equation

HRID 2272455 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:8][CH3:9].CN(C=O)C.[CH:15]1([C:19]2[C:28]([CH:29]3[CH2:31][CH2:30]3)=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([OH:32])[CH:20]=2)[CH2:18][CH2:17][CH2:16]1>O>[CH:15]1([C:19]2[C:28]([CH:29]3[CH2:30][CH2:31]3)=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([O:32][CH2:8][CH3:9])[CH:20]=2)[CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 90424074HCID 90424074, compound

Product 1

HCID 90423560HCID 90423560, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cesium carbonate (3.44 g) and iodoethane (0.55 mL) were added to a DMF (25 mL) solution of methyl 4-cyclobutyl-5-cyclopropyl-2-hydroxybenzoate (1.3 g) under ice cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with water, followed by extraction with ethyl acetate twice. Combined organic layers were washed with water and saturated saline in this order and dried over anhydrous sodium sulfate, and then, the solvent was distilled off under reduced pressure to obtain the title compound (1.2 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate twice
  2. washCombined organic layers were washed with water and saturated saline in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2d0e058d192f4f928a8d4bfc7f45d081
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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