Triethylamine → HCID 59570198, compound

HRID 2071085Notes

Reaction equation

HRID 2071085 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)[CH:5]=[O:6].[N:13]1([C:19](Cl)=[O:20])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:13]1([C:19]([O:1][C:2]2[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=2)=[O:20])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 574477143-Hydroxy-5-(propan-2-yl)benzaldehyde

Product 1

HCID 59570198HCID 59570198, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 91.9 mg (0.634 mmol) of 3-hydroxy-5-isopropylbenzaldehyde in 5 mL of CH2Cl2 at r.t. was added 220 μL (1.92 mmol) of 4-morpholinecarbonyl chloride and 0.5 mL (3.59 mmol) of Et3N. After 3 h, sat. NaHCO3 (15 mL) was added, and the aqueous layer was extracted with CHCl3. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (20% EtOAc/hexanes) provided 38.8 mg of 3-formyl-5-isopropylphenyl morpholine-4-carboxylate as a yellow oil in 24% yield.

Workup

  1. extractionthe aqueous layer was extracted with CHCl3
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash silica gel chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7448569029574273b4f26fcce7c349df
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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