Diethyl Oxalate → HCID 18694144, compound

HRID 399907Notes

Reaction equation

HRID 399907 reaction equation
C[O-].[Na+].[C:4]([O:11]CC)(=[O:10])[C:5]([O:7][CH2:8][CH3:9])=O.[OH:14][C:15]1[C:23](C(=O)C)=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][CH2:18][CH2:19]2>CC1C=CC=CC=1>[O:14]=[C:15]1[C:16]2[CH:17]=[CH:18][C:19]3[CH2:20][CH2:21][CH2:22][C:9]=3[C:8]=2[O:7][C:5]([C:4]([OH:11])=[O:10])=[CH:23]1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 10942334Sodium MethoxideHCID 186941771-(2,3-Dihydro-4-hydroxy-1H-inden-5-yl)ethanone

Product 1

HCID 18694144HCID 18694144, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Sodium methylate (24 g) was stirred in methylbenzene (300 ml). A mixture of diethyl oxalate (0.16 mol) and intermediate (2-a) (0.16 mol) in methylbenzene (10 ml) was added dropwise. This mixture was stirred and refluxed for 2 hours. The resulting precipitate was filtered off and dried. The solid was stirred in a mixture of hydrochloric acid (10 ml) and acetic acid (500 ml). The reaction mixture was stirred and refluxed for 1 hour. The mixture was poured out into water. The resulting precipitate was filtered off and dried (vacuum), yielding 21 g of 4,7,8,9-tetrahydro-4-oxocyclopenta[h]-1-benzopyran-2-carboxylic acid (interm. 3-a).

Workup

  1. additionwas added dropwise
  2. temperaturerefluxed for 2 hours
  3. filtrationThe resulting precipitate was filtered off
  4. customdried
  5. stirringThe solid was stirred in a mixture of hydrochloric acid (10 ml) and acetic acid (500 ml)
  6. stirringThe reaction mixture was stirred
  7. temperaturerefluxed for 1 hour
  8. additionThe mixture was poured out into water
  9. filtrationThe resulting precipitate was filtered off
  10. customdried (vacuum)

Sources & evidence

ORD record
ord-d8c996f14e0845e68c933c0fc8c84a93
Source dataset
uspto-grants-1998_10
Patent number
US05824682

Reaction notes

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