153787-16-7 → Ethyl 3,4-dihydro-2H-1-benzopyran-3-carboxylate

HRID 1446385Notes

Reaction equation

HRID 1446385 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH:3]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]>[Pd].C(O)(=O)C>[O:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][CH:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:4]1

Participants

4

Reactant 1

HCID 67239220153787-16-7

Product 1

HCID 53408537Ethyl 3,4-dihydro-2H-1-benzopyran-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-oxochromane-3-carboxylic acid, ethyl ester (4.0 g, 18 mmol) and 10% palladium on carbon (0.4 g) in 100 mL of acetic acid was degassed and filled with hydrogen using a balloon. After stirring at 70° C. overnight, the reaction mixture was filtered through CELITE diatomaceous earth, and the CELITE cake was washed with ethyl acetate (200 mL). The filtrate was washer with water (2×200 mL), dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.2-7.0 (m, 2H), 6.84 (t, 1H), 6.74 (d, 1H), 4.36 (dd, 1H), 4.21-4.13 (m, 3H), 3.03 (m, 3H), 1.26 (t, 3H).

Workup

  1. customwas degassed
  2. additionfilled with hydrogen using a balloon
  3. filtrationthe reaction mixture was filtered through CELITE diatomaceous earth
  4. washthe CELITE cake was washed with ethyl acetate (200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1a58fc77b5cb46c293db5f2016ceaaf3
Source dataset
uspto-grants-2010_02
Patent number
US07667053B2

Reaction notes

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