Salicylaldehyde → 3-formyl-2H-chromene-2-carboxylic acid ethyl ester

HRID 1925927Notes

Reaction equation

HRID 1925927 reaction equation
C1(C2(CO)CCCN2C2C=CC=CC=2)C=CC=CC=1.[N+](C1C=CC=CC=1C(O)=O)([O-])=O.[OH:32][C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1[CH:35]=O.[CH2:41]([O:43][C:44](=[O:49])/[CH:45]=[CH:46]/[CH:47]=[O:48])[CH3:42]>C1(C)C=CC=CC=1>[CH2:41]([O:43][C:44]([CH:45]1[C:46]([CH:47]=[O:48])=[CH:35][C:34]2[C:33](=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:32]1)=[O:49])[CH3:42]

Participants

6

Reactant 4

HCID 6998SalicylaldehydeHCID 110872-Nitrobenzoic acidHCID 7019541Ethyl (2E)-4-oxo-2-butenoateHCID 19046280Diphenyl-2-pyrrolidinemethanol

Product 1

HCID 238182513-formyl-2H-chromene-2-carboxylic acid ethyl esterYield 29%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred mixture of commercially available (S)-(−)-α{tilde over (α)}Diphenyl-2-pyrrolidinemethanol (0.83 g, 3.28 mmol) in toluene (40 mL) was added 2-nitrobenzoic acid (0.55 g, 3.28 mmol), commercially available 2-Hydroxybenzaldehyde (2.00 g, 16.38 mmol) and (E)-4-oxo-but-2-enoic acid ethyl ester (2.51 g, 19.65 mmol). After addition was complete the mixture was stirred at room temperature for 3 days. Upon completion of the reaction the toluene was removed by vacuum distillation. The residue was diluted with ethyl acetate and washed with water, a saturated sodium bicarbonate solution and a saturated sodium chloride solution. The organic fraction was then dried over magnesium sulfate. The crude product obtained was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; (0% to 100% ethyl acetate/hexane) to afford 3-formyl-2H-chromene-2-carboxylic acid ethyl ester as a yellow oil, 1.09 g (29% yield). (Ref: Chem. Eur. Journal; 2007, 13, pg 574).

Workup

  1. additionAfter addition
  2. customwas removed by vacuum distillation
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic fraction was then dried over magnesium sulfate
  6. customThe crude product obtained
  7. customwas purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g

Sources & evidence

ORD record
ord-6516d5d52c7a4218bfebadb2f0c1d4a7
Source dataset
uspto-grants-2012_05
Patent number
US08178689B2

Reaction notes

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