Methanol → (+/-)-Dimethyl 2-(2-oxoethyl)-1,2,3,4-tetrahydronaphthalene-2,6-dicarboxylate

HRID 133122Notes

Reaction equation

HRID 133122 reaction equation
[CH2:1]([C:4]1([C:18]([O:20][CH3:21])=[O:19])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[CH:10]=2)[CH2:5]1)C=C.I([O-])(=O)(=O)=O.[Na+].[CH3:28][OH:29]>O.[Os](=O)(=O)(=O)=O>[O:29]=[CH:28][CH2:1][C:4]1([C:18]([O:20][CH3:21])=[O:19])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[CH:10]=2)[CH2:5]1

Participants

6

Reactant 3

HCID 887MethanolHCID 23667635Sodium periodateHCID 67526596(+/-)-Dimethyl 2-allyl-1,2,3,4-tetrahydronaphthalene-2,6-dicarboxylate

Product 1

HCID 86616923(+/-)-Dimethyl 2-(2-oxoethyl)-1,2,3,4-tetrahydronaphthalene-2,6-dicarboxylate

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of (±)-dimethyl 2-allyl-1,2,3,4-tetrahydronaphthalene-2,6-dicarboxylate from Step B (433 mg, 1.50 mmol) in MeOH (20 mL) and H2O (7 mL) was added osmium tetroxide (2.5 wt. % in t-BuOH, 1.07 mL, 0.105 mmol) and sodium periodate (964 mg, 4.51 mmol). The resulting mixture was stirred for 1 h at ambient temperature and a thick white precipitate quickly formed. After 70 min, the mixture was partitioned between dilute aqueous NaCl (100 mL) and EtOAc (200 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound in sufficient purity for use in the next step. MS: m/z=291 (M+1).

Workup

  1. customa thick white precipitate quickly formed
  2. waitAfter 70 min
  3. customthe mixture was partitioned between dilute aqueous NaCl (100 mL) and EtOAc (200 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-686d869e4b8e46f4bb5b7f7c4db207c2
Source dataset
uspto-grants-2008_06
Patent number
US07390798B2

Reaction notes

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