Potassium sodium tartarate → HCID 67690524, compound

HRID 1078699Notes

Reaction equation

HRID 1078699 reaction equation
[C:1]1([CH:7]=[C:8]2[C:13](=[O:14])[C:12]3[CH:15]=[CH:16][C:17]([CH2:19][C:20](OC)=[O:21])=[CH:18][C:11]=3[O:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[OH:14][C@@H:13]1[C:12]2[CH:15]=[CH:16][C:17]([CH2:19][CH2:20][OH:21])=[CH:18][C:11]=2[O:10][CH2:9][C@H:8]1[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 53884247HCID 53884247, compound

Product 1

HCID 67690524HCID 67690524, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-phenylmethylene-7-methoxycarbonylmethyl-2H-1-benzopyran-4-one (4.2 g, 14.3 mmole) in THF (70 ml) at 0° C. was added lithium aluminum hydride (2.16 g, 57.1 mmole) portionwise over 10 minutes. The mixture was slowly warmed to room temperature then heated at reflux for 5 hours. The mixture was cooled to 0° C. and 200 ml of saturated sodium-potassium tartrate solution was carefully added over 10 minutes. The mixture was stirred at room temperature overnight, the clear organic phase separated and the clear aqueous layer extracted with 2×100 ml of ether. The combined organic layers were washed with water and brine then dried over MgSO4. Filtration followed by evaporation in vacuo and chromatography (silica gel 2:1→1:5 hexane:ether) gave 2.61 of the title compound (64% yield).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 5 hours
  3. temperatureThe mixture was cooled to 0° C.
  4. customthe clear organic phase separated
  5. extractionthe clear aqueous layer extracted with 2×100 ml of ether
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialthen dried over MgSO4
  8. filtrationFiltration
  9. customfollowed by evaporation in vacuo and chromatography (silica gel 2:1→1:5 hexane:ether)

Sources & evidence

ORD record
ord-871f5224043141a5be6487c1dd2fe048
Source dataset
uspto-grants-1996_08
Patent number
US05550152

Reaction notes

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