HCID 19372339, compound → HCID 10712813, compound

HRID 129696Notes

Reaction equation

HRID 129696 reaction equation
OC([C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[CH:7]=[C:6]([C:22]([O:24][CH3:25])=[O:23])[CH:5]=1)C.C[C:27]([CH3:29])=[O:28].[OH:30]S(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:22]([C:6]1[CH:5]=[C:4]([CH2:29][C:27]([OH:30])=[O:28])[C:13]2[C:8]([CH:7]=1)=[CH:9][C:10]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:11][CH:12]=2)([O:24][CH3:25])=[O:23]

Participants

4

Reactant 2

HCID 19372339HCID 19372339, compoundHCID 131709961Jones' reagent

Product 1

HCID 10712813HCID 10712813, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.08 g (0.24 mmol) of 1-hydroxyethyl-3-carbomethoxy-6-benzyloxynaphthalene in 10 ml of acetone at 0° C. is added Jones reagent until a green precipitate forms. After stirring at 0° C. for 10 minutes, the mixture is partitioned between ethyl acetate and H2O. The organics are dried (MgSO4) and concentrated in vacuo to afford 0.081 g of 3-carbomethoxy-6-benzyloxy-1-naphthyl acetic acid in the form of a light tan solid which is used directly in the next step.

Workup

  1. customthe mixture is partitioned between ethyl acetate and H2O
  2. dry with materialThe organics are dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6d30e4bb6f0457993ca5a2a4f7ea51f
Source dataset
uspto-grants-1995_11
Patent number
US05468898

Reaction notes

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