Sodium Bicarbonate → HCID 54226052, compound

HRID 2231905Notes

Reaction equation

HRID 2231905 reaction equation
[C:1]([C:4]1[C:5]([OH:23])=[C:6]([CH2:20][CH2:21][CH3:22])[C:7]2[O:12][C:11]([CH3:18])([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9][C:8]=2[CH:19]=1)(=[O:3])[CH3:2].O.[C:25]1(C)C=CC(S(O)(=O)=O)=C[CH:26]=1.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:25]([O:16][C:15](=[O:17])[CH2:14][CH2:13][C:11]1([CH3:18])[CH2:10][CH2:9][C:8]2[CH:19]=[C:4]([C:1](=[O:3])[CH3:2])[C:5]([OH:23])=[C:6]([CH2:20][CH2:21][CH3:22])[C:7]=2[O:12]1)[CH3:26]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 14329718HCID 14329718, compound

Product 1

HCID 54226052HCID 54226052, compoundYield 385.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 692 mg of racemic-6-acetyl-3,4-dihydro-7-hydroxy-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid and 100 mg of p-toluenesulfonic acid monohydrate in 10 ml of absolute ethanol was stirred and refluxed for 17 hours. The resulting solution was cooled and treated with a small amount of saturated sodium bicarbonate then concentrated in vacuo to remove the ethanol. The residue was treated with ether and the ether solution was processed in the usual manner given 752 mg of a yellow oil. This material was chromatographed on 50 g of silica gel. Elution with 4:1 toluene-ethyl acetate provided 706 mg (92.9%) of racemic-6-acetyl-3,4-dihydro-7-hydroxy-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid ethyl ester as a yellow oil.

Workup

  1. temperaturerefluxed for 17 hours
  2. temperatureThe resulting solution was cooled
  3. concentrationthen concentrated in vacuo
  4. customto remove the ethanol
  5. additionThe residue was treated with ether
  6. customThis material was chromatographed on 50 g of silica gel
  7. washElution with 4:1 toluene-ethyl acetate

Sources & evidence

ORD record
ord-0d7c184b9aef49bea7238d75a2eb7a95
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

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